there is some very good advice here, choose what is applicable to your circumstances.
For what it is worth, do not be so quick to discount trailerables, they can be slipped like any other boat and if it is the one you plan to sell when you upgrade, it is easier to sell and does not have monthly slip fees to pay while on the market for sale. Also if you start small and then upgrade be absolutely sure it is popular and resellable, there is a reason why there are so many boats for sale these days. Do some demographics research, a real eye opener, many baby boomers entering retirement age. When they sell their boats in a few years the markets will be flooded, you will have trouble selling any boat, there simply aren't enough younger buyers out there and what ones there are come from the instant gratification generation and they buy powerboats. A bit of demographics research will tell you that any sailboat you buy is going to be a white elephant later on, so plan to keep it, or have it inherited. One more thing, if you unexpectedly become financially squeezed, that monthly moorage fee is going to be the first expense you want to divest yourself of and few others will want to assume it, depending on the economic climate, that is where trailerables have the advantage.