dr:
Ultimate plan is for the wife and I to be able to 'bug out' from work and 'escape' in the decade or so to the run up to 'retirement'. We are both feeling the pressure of being 'maxed out' in the seniority of our jobs... senior stuck as it were

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So being able to load the pups, food and just head out when her schedule and mine overlap for three or four days at a stretch on the 'big' boat. We are mulling over her having a camper trailer and I getting a boat. We then just decide, hit the store, and go for a trip overland or over water

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As for the short term training boat, I think I'd be happy with a day boat cause I would just take a tent and camping gear like when I was a pup if I wanted a weekend. Wife don't ken that too much, so if a day boat, it will be to destinations we can 'room' at. Mostly it would be me getting back on the water.
It would be around the Chesapeake, but at some point it after getting out of the rat race it would be nice to do a 6 months trip down to Fl via the intercostal.
This is all squishy, cause we are still pushing this around.
Ill buy used. I be handy with tools and have 'worked' on boats before, so that might be something a bit more rough that get worked on till it is ready to use. Big boat would be around $25k ish (cost of a used camper).
I need to nose around the classifieds cause I am way out of touch to what money buys anymore.