www.iFourWinns.com

Not familiar with that boat but will add that I would suggest a survey, especially if there is hull damage. Any water intrusion could mean rotten wood which is a major deal.

You need a good survey that will check for moisture content on the stringers, transom, etc...
Make sure 100% of everything on the boat works. Survey will do this once the boat is in the water.
Look at condition of wiring (has it been hacked up).
If things are now working and you are constantly having to fix stuff, your wife/kids are not going to be happy. One breakdown on the water will ruin it for them.

Trailer - you can buy a new aluminum I-beam trailer for about $5000.00 for that boat. I would not buy used unless you get lucky and find one in really great shape. Then your probably looking at new tires and bearings so you know personally the condition.

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The Dance II
2007 278 Vista
6.2L Mercruiser

Survey, survey, survey! Very helpful in finding out the overall condition of the boat. My insurance company also required a copy of the survey. I also had a mechanic check out the engine. He was able to hook the computer up to it and check for codes. Also told me exactly how many hours it had been run at different RPMs.
Check if the current owner has maintenance records and/or find out where he had work done on it. I did this and went and talked to the shop. Good idea to find out if the drive has been maintained correctly over the years.

I was originally looking for a 268 when I bought my boat. It was not easy finding any with trailers and a new trailer wasn't in the budget. The 248s on the other hand seemed to all have trailers with them.

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2004 248 Vista "Amante"
MC 5.0MPI/B3

From what I could tell you gain about 6-8" in the cabin. The galley has a little more storage space and the "closet" between the head and the aft cabin is bigger.
The cockpit is the same size in the 268s and 248s. The 268s had the arch option and the 248s did not.

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2004 248 Vista "Amante"
MC 5.0MPI/B3

If the bilge was dry before look for water leaks around the transom
Does the boat sit level or does it list?
Engine starts and runs well?
Engine temp & oil press & volts normal? (Ie 160-175, oil press 40-60 running, volts 13.5-14)
Does it reach max rpm wide open? (4600 or so)?
Drive shifts well?
No VIBS when trimming or steering?
Check riser joints for leaks and rust....

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88 Four Winns 200 Horizon
4.3 OMC Cobra-4bbl
2002 Walker Bay 10/2012 Suzuki 2.5
2008 Walker Bay 8

1998 Jeep Grand Cherokee 4.0/Selectrac
2007 Jeep Grand Cherokee 5.7 Hemi/Quadradrive II