Oh, and don't underestimate how much your new boat will need in upgrades.
Here in Oz i learned that most boats in this size range (25' to 32') have spent their lives as day sailers and racers, with the occasional weekend away.
Thus they need quite a bit of gear
to effectively convert them to all-weather bluewater cruisers. Mine needs: Storm sails
, drogues, bigger anchors & rodes, tougher reefing gear
, more water storage
, bigger electrical
capacity, lee cloths for the berths, windvane
(though i think i'll run my auto helm
until it dies, while saving for a windvane), and on the list goes.
I agree with an earlier post that staying in your house, having your boat in the front yard and working on her in your spare time would indeed be ideal.
But i decided to go the liveaboard
and upgrade route
myself, which is more difficult, but suits me okay so far.
The other factor for me was this: I had done a great deal of reading (wannabe dream-fodder reading) and had developed preferences, or perhaps they are better to be called prejudices. Things i thought i must have, and certain ways of doing things, different gear i wanted, etc... All based on the reading of other sailors, and their preferences.
Then as i got into a bit of sailing in trailer sailers, i realised that everyone's preferences are different, and 'my' preferences weren't mine at all - they were other peoples'.
So i now favour the strategy of getting a capable boat and going sailing. And just plain coping with what appear to be its inadequacies.
Then decide on the basis of your own EXPERIENCE what changes and upgrades you'll need.
And I follow Rebelheart's advice about being ruthless in differentiating 'needs' from 'wants'.