You won't find soft spots in a deck in 20 degree weather...the water that is encapsulated in the soft spots is currently ICE and makes the whole deck seem solid. Even a moisture meter won't detect water in these conditions, since it won't detect ICE very well.
As for the deck paint job, it sounds like the deck paint job wasn't prepped very well, and 95% of the effort and cost in a good paint job is the prep. When painting a deck and cabintop, it really makes much more sense to remove all the hardware possible, as that allows you to get a paint job with fewer exposed edges that can be starting points for the job failing.
I'd point out that if the paint job was done so poorly, that likely indicates that little care was given to the other maintenance tasks and repairs on this boat. The boat is likely to be in need of some major maintenance, if not outright repairs...
If you haven't read the Boat Inspection Trip Tips thread I started, I would highly recommend you do so before continuing further.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.