After looking at boats for a couple of months I think $5k is a real stretch for what you want
I bought a Pearson 30 in sailable condition for $4,000. Dry hull and deck with no core rot. Everything worked. I put money into it because I wanted
to not because I had to.
A friend of mine bought a Pearson 30 that was 800 hulls newer for about $800 more, that is just as dry, just as solid, that had WAY more convenience features than mine came with. (Roller furling, Force10 heater, pressurized water, wheel steering, auto-pilot, decent sails, all for arond $5,000).
Another friend just bought a Pearson 30 a couple of weeks ago for $2k or $3k.
Everything works, but it does have a delaminating area on the cabin top that we'll re-work next winter.
A 27 footer in decent shape can be had for $5,000 if you're a careful shopper.
I agree with the posted recommendations:
Abin Vega 27 (This one's bomb-proof but a bit cramped compared to the others. Good for off-shore work)
Tartan 27 (Also tough, but a bit cramped. Old school)
Cal 27 & 28
Cape Dory 27 (Another slow, cramped, but very tough design. Sea-kindly)
I might even throw in a Coronado 27, but I wouldn't go far offshore in it.
With all of those choices, you should be able to find SOMETHING good in the current boat market.