Early Retirement Extreme Forums

I've mentioned a few times that one of my plans in ERE is to live in a warm climate (SW Florida) during the winter months (Nov-May) and live up north with my family during the summer. I think it's a great plan to get the best of both worlds and hopefully live cheaply in the north when summer hits.
My question is this:
I have a few different ways of going about this.
1. I could rent a cheap room or apartment while I'm in Florida. It would have to be a seasonal or month-to-month rental. These can sometimes be difficult to come by if they're not by the beach, and they usually come at a premium due to the short-term lease. In the summer I could stay stress free up north, not having to worry about any possessions or property down south.
2. I have thought about purchasing a cheap 2 br condo around $70K and renting out the second bedroom right away to help build my equity and also once I enter ERE continue renting out the second bedroom. This would keep my condo occupied and hopefully safe while I spend the summer up north. The problem would be with trust. While I'm spending 4-5 months up north I wouldn't be around the roommate...so I couldn't be there in case something happens, or they up and walk away with all my stuff. So..there would be a stress factor there. Also, until the place is paid off I'd be paying on it while I'm supposed to be living up north cheaply. Even with the rent there would still be costs above and beyond the rent for the mortgage, HOA, taxes, etc.
3. I could RV it. I could keep the RV in the driveway at my parents place when I stay up north and keep it an RV park down here in FL in the winter. This is the least desirable and least realistic option for me. But, I figured I'd throw it out there.
Any opinions from the crowd? I know there are some very creative people on this board, so maybe there is something I haven't considered?

In ERE, you have the advantage of not needing to live at any one particular location. So if you location parameter is "SW Florida", I'd be willing to bet that you can find a seasonal rental somewhere in that location. I live in a small city and can find about 10 short-term rental listings per day. Expanding the location to a hundred square miles should net you at least a few options (-:
Consider rentals near universities too: they will be more likely to be part-year leases if their primary tenant market is college students. Plus, they tend to be located near things.

Your 3 options are probably the most practical. Here are a few other ideas:
You could buy a duplex/triplex and have a management company rent out the unit(s) besides yours. That way you have an "agent" in town representing your interests, and your personal effects are under lock and key.
You could buy a house near a university and rent to students, with the understanding that they move out for the summer.
You could buy a multi-unit property and have a management company handle renting it out while you're gone.
There are other mobile dwellings besides RVs: boats, mobile homes, yurts, shipping containers, etc.

I agree with Chris. I think you'll find plenty of short-term rentals; close by the beach or off the beach. Many are furnished. Prices will vary widely depending on size, quality, amenities, and location. You'll probably pay a slightly bit more than a year-round lease, but if you can show that you're a very responsible tenant, most small-time landlords will go out of their way for you, especially if you're a repeat customer.

I think it would be a dream come true to have two small, efficient places, and move between them at will to follow the nicer weather.
The problem seems to be the cost, particularly for the Florida residence. For example, if you planned to live on $750/mo in ERE, you might feel that you need 400x this in order to retire, thus $300k. If the florida place ends up costing you an additional $200/mo in insurance, hoa, taxes, and maintenance, then you'll need another $80k to cover this, and that doesn't include the purchase price. You may be able to push your monthly expenses down from $750, but I think it's pretty hard to own a condo in florida without generating around $200/mo in expenses-- the HOA and taxes often get to $150/mo, even on properties selling for under $50k.
You might be able to get the monthly cost of ownership down to around $100/mo in certain areas by not insuring the residence and not being part of a HOA. For instance you could buy a piece of land outside of an HOA and put a mobile home on it. If you don't insure the mobile home, you'd really only have property taxes and maintenance to cover. Though places without HOAs that allow you to put a mobile home on them are often farther from bus lines, shopping centers, etc...
So, your plan to cover your monthlies by renting out part of the place seems good to me, particularly if you own the condo. I think you could eventually find a really suitable roommate-- it's actually a great deal for them. It might be a hassle to find the right person initially though.
A traditional RV would seem to burden you with expenses too-- registration, insurance, maintenance, lot fees, and horrible gas mileage. A stealthy class B or van-living type situation might cut the costs a lot.
I think the cheapest way to go is to minimize your belongings such that you can easily move from one low cost rental to another.

I'm considering the same options, though with the twist that we actually want to live somewhere with more winter instead of less (ski towns) so the RV wouldn't work out as well. I don't mind a bit of landlording in the future because I'm doing that now with my old house in Atlanta without too much trouble. Here's what we did this year:
Winter: Rented a 3BR apartment in the Rockies Nov-Apr and partially paid for the rent by doing short-term rentals to vacationers. DH was also able to work at a ski resort for free passes and some extra income. I'd imagine you could do something similar at a beach resort kind of place in Florida?
Summer: Staying with friends for free in Detroit May-Sept. We have a great set up now, but I don't want to be dependent on someone else's generosity for housing the rest of my life. Also, I'd like to have my own home to set up a workshop and garden.
This winter we're aiming to do the ski resort thing again, but in New England.

I've been thinking about something similar. Summer in Maine, near a college town. Buy a small place with bare bones. Rent to a student during fall and winter.
Fall and Winter in Arizona. Lots of cheap places right now. I'd just lock it up for the summer and leave behind the triple-digit heat.
The trip between would be a leisurely motorcycle/camping adventure on different blue highways each year.
Probably not the cheapest ERE plan, but the logistics will keep me mentally sharp.

One thing to consider is the homestead side of the equation. If you're official residence is in FL and you summer in the north, you will likely have lower income taxes and health care. Also you're expenses on your owned dwelling (if you take that approach) will be lower (winterization, taxes, upkeep, all higher in north).
One approach I've considered is to own in FL nearish to the beach, then RV to the north for a seasonal spot. I think Mo is right in that it's going to be tough to be really cheap - but it may be worth some extra expense given the benefits. To build on something @S mentioned.... if you could rent your FL home even a few weeks of the peak season to off set expenses, if you had an RV, you could stay in that whenever you were able to rent the house.
Another possible option for summer rentals in the north is furnished studio condos at small local ski areas. I've seen some of these deals in new england that seemed like they'd be great for far cheaper than you could otherwise rent, and they are short term seasonal.

@chilly Even if you don't spend most of your time in a tax-advantaged state, you may be able to claim residency elsewhere. For instance, I'm a SD resident. There's no state income tax and you can do almost of your dealings with the state by mail. Also, insurance and vehicle registration stuff is very cheap. When we bought our truck, it only cost $12 to register it with the plates we already had. In general if you live somewhere less than 6 months of the year and don't have a job based there, you don't have to become a resident. I'm not a lawyer or accountant however, so take legal advice from people on internet forums with a grain of salt. We use these guys and they're great: http://www.mydakotaaddress.com/

I thought of another good way to live somewhere nice during the peak few months of the summer.... college sublets. Lots of nice college towns where you could escape at least July and August in the south.
@S, that's an interesting site. I've heard of services like that in NV. I'll have to look into it, although I don't think I'd dare try it somewhere I had no real ties to at all... but who knows after checking into it some more.

To revive this thread vis-a-vis choice of residence. Some good ideas here on what, weather arbitrage?
In childhood, knew a housepainter who ran a snowbird route from NH to FL every year. In summer, he'd drive around certain areas visiting builders and RE agents looking for work. He was an excellent painter, and could blend any color you could imagine (pre-zillion paint chips) and prime and paint a new house within a week using only brushes and a ladder. He lived out of his station wagon some of the time, taking a temporary apartment when he was in pocket, and keeping his few brushes and tarps in the bay and keeping a ladder on the roof.
When it started to turn cold, he'd drift south, repeating the work-getting process until he wound up in FL by January. He didn't mind the cold so much as he hated competing for indoor work in the winter. He also hated checks, until he opened a bank account in the name of Jack Manure. The teller thanking him by name for his business delighted him.

I like option three the best, if only b/c I'm thinking of the same thing:)
Option two seems less desireable, as Mo mentioned, due to year around expenses with only partial year residence. This could be offset with a roomate, but it still seems like the expenses would get you unless you could really reduce the initial cost of the condo.
Option one is probably your best if you really don't like the RV idea.

I do live in two places, one in the Netherlands and one in Austria for skying and sun in the winter. (I wrote about it, see forum INSPIRATION: living as an aristocrate). I don not use a car in Austria so I travel light between the two countries by cheap airplaneflights.

The smal condo in Austria is very well maintained by the owners association of ca 40 members. The house in the Netherlands I maintain myself. I run both for less than € 600 per month, inclusive heating, electra, television, telephone and insurance. There are of course no loans.

My parents used to do the snowbird thing. They always seemed to find either a beachside motel (no maid service, usually a minimum of 2 or 3 months) with a kitchenette for $700 per month, and a few times they found a condo for short term rent for slightly higher (could be shared as there was at least 2 bedrooms). They had to be out my March break though.

Owning a place requires maintenance and taxes and someone to watch it when you are not there. Look for smaller towns that perhaps are touristy in the summer, but are thankful of any business in the winter.

I do this. I own two places and travel between them. Both are triplexes and one is on the west coast and the other in the interior - approximately 400 km apart.
I run one as a weekly vacation rental in the summer (it is a vacation spot) and on cheaper leases in the winter - retaining one unit for my use in the winter as I work in that location one week a month and my parents live there. It makes approximately $600/month net while the mortgage is being paid down.
The other unit in the triplex on the coast is our permanent home. The rent is subsidized by the other two units and we end up paying about $600/month including ownership costs and don't rent it out when we are not there - although we may do that one day.
Overall we pay nothing for housing except the lost opportunity costs on our down payments, which I consider good value even if prices drop because of equity paydown by other peoples money in the form of the rental payments.
I think it is a good plan but you should try to think about all the variables including break-even points and the hassles of ownership.

I once had a landlord in a bigger student city that did it a bit like option 2: he owned that place and it had three upstairs rooms (with bathroom) and a downstairs living-room/ open kitchen with guetst-toilet. He took the smallest of the upstairs room and a friend and I rented the other ones.
So basically we paid for his rent and were concerned about upkeep and he would phone one week ahead of when he would come. Mostly he stayed for two to three weeks and took over the living room but we got on togehter quite great. Otherwise he lived in another country in another big town.

Your decision is affected by how many personal belongings and pieces of furniture you have and how much you can afford in rent. Option 1 - renting a room or small apartment for 7 or 8 months each winter season - requires you to store your FL belongings while away for the summer, then retrieve them when you're back to FL. And do you look for a new 8-month rental each winter or make arrangements to continually re-rent the same spot? You'll pay a premium for leases that are less than one year. I'm familiar with S. FL and there are plenty of beachfront studios and small apartments that do this, and have rented to the same northerners for decades.
A better idea might be to simply rent a decent studio or small 1 bedroom to your liking on a year-round basis, forget about a roommate, and simply lock it up for the 4 months you're gone.