You're in FL, right? Does house A's neighborhood have a lot of foreclosures?
House B sounds like a winner. 5 minutes to the beach and downtown has a LOT of value. Jobs come and go, but the beach ain't movin'.
I wouldn't call 2000 sq ft a ton of space (me, my wife, and 4 cats fill it pretty well with all our crap), but it's certainly not crowded for the average family.
And does B have space to expand the garage? Build a workshop/bike storage/detatched? A regular 2-carhole leaves zero room to boogie. But if you don't have to deal with HOA bullshit and have at least a bit of land, there's potential.
I would guess that house A is new/recent construction, and B is older, maybe 80s? New construction in boom areas tends to be of shit quality, but tropical weather ages stuff quickly.
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