Do you think a third boat might need to be added to the list. Something small cheap and with budget you could consider it disposable. You can find em anywhere. Sail it till you find the right boat then put it on Craigslist and let the first person that shows up with cash take it off your hand. There are a lot of nuances to sailing that can really only be learned on a small boat.
Something like this sail the snot out of it for a year and it is a throwaway on your budget but should resell easily.
26' Sailboat Chrystler '79