I would definitely recommend transferring cash ISAs to Stocks and Shares. I had to pay a transaction fee to do so, which was 1% of the amount. Can you recommend a good Cash ISA? I just got a statement for one of my Cash ISAs and it paid less than 1% interest this year! It was paying much more than that last year and they never informed me of the rate change.
I'm happy to keep some money in Zopa because it is a small amount compared to other investments (about £5K). I consider it an experiment and am prepared for the possible downside as well as upside.
My market timing involved a lot of luck. I'm afraid I don't have any secret techniques. I bought the flat in 2001 very cheaply (£23.5K)as soon as I had a permanent job that paid enough to get a large enough mortgage to buy a place. In 2001 the housing market in that part of Scotland was still very much a buyers market: it didn't really take off until 2005.
People warned me not to buy, because the market was so bad and the city population was falling and I was buying all I could afford, which was a 1 bed flat in a bad part of town which they thought I might never be able to re-sell. My argument was that a) I was going to be there at least 3 years b) the mortgage was 30% cheaper than renting a comparable place, and was even slightly cheaper than getting a room in a shared house and c) even if the market never recovered, if I was moving it would be because I had a much better job offer in another part of the country, or had paid off the mortgage, so either way I could rent it out for below market rate and it would not cost me anything.
5 years later I had to move to a different city for work, and the market in the old city was just starting to take off. I had also paid off most of the mortgage, and the new city was so much more expensive that selling the flat would make little difference to how much house I could afford there, so I kept the flat and rented it out.
My tenant was okay at first but then his income became more precarious (he was self-employed) and he was often very late paying the rent, so I decided not to give him a new contract after the 2nd year and sell the flat instead, in order to avoid Capital Gains Tax, which would have kicked in if I rented it for a further year before selling. I also realised that the capital appreciation over those 2 years was unsustainable and my luck was likely to run out sooner rather than later.
I did think the housing market was stalling, and actually it was pretty bad by the time I put my flat on the market, but I got lucky and managed to sell quickly (2 weeks) and had 2 interested parties which pushed the price up to what I wanted.
I've not been so lucky with my current house. It is worth what I paid for it, but no appreciation in 5 years (actually it appreciated 25% then deflated back to the price I paid for it). The mortgage is cheaper than private rents though, so it isn't a disaster.
In terms of the stock market, I tend to start buying when the FTSE has dropped below 4,500 and colleagues are telling me "Never catch a falling knife". The market then drops further and they say "I told you so." But then it rebounds back much higher, and stop commenting. I'm not sure which way it is going to go next, but I'm investing about half my stocks and shares allowance in timber, natural resources and green energy funds, as well as trackers for China, Brazil and India, so half of it is not on the FTSE.
I'm still buying stocks, but am trying to work out when the best time is to stop buying (or at least reduce the amount I am buying) and start stockpiling cash to buy another flat to rent out. Market timing seems to be much more important with property than with the stock market because you can drip feed money into the stock market but you can't do that with property, unless you are so rich that you can afford to buy several properties.