If I was in the market in your range, I would be looking for 18-19 ft I/O with a 115 -150hp Johnson/Evinrude V-4 outboard. There are tons and tons of these V4's around, they have good reliabiltiy and can be swapped very easily. Maybe even a deckboat configuration, although those are rare in that age group.
OK, now researching pros & cons of an outboard in the 19'-20' range...I know this question has been asked and answered so I won't bother repeating it here, unless anyone has strong feelings they'd like to offer.
I am finding folks say that OBs are less maintenance heavy but harder to work on. Well, I have built more auto engines and transmissions than I can remember, and have retrofitted electronic fuel injection to two auto engines, one which I autocrossed with moderate success (car was faster than driver). I am in the machine tool industry and am well-tooled (I mean, I have lots of tool; i.e, mill, lathe, press, MIG, etc.) I don't reckon it will be beyond me, but again advice is welcome.
Rear weight bias is something to consider esp. towing skiiers, wakeboarders, etc.
Your help has been fantastic. Back with more questions soon I'm sure,
Ron
IThat engine also has the Vortec heads, which I believe came out in 1994. Could be wrong on the year there. It also has the Alpha 1 outdrive.
Also I've been told that the performance between the 4.3 and the 5.0 isnt that much different, and to really see an increase you need to get the 5.7 (350).
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This boat would tow your son our of the water just fine with a lower pitch prop: Stingray ski boat (Winchester)
Also, if you keep looking and wanted to spend just a little more, I think you can find the 19 foot stingray with a 4.3 for just a grand or so more. Search on the 190 LX or 190 LS. 8 adult capacity, pretty light for an 19 foot boat, and nice and roomy, with lots of storage space.
It is the boat I have!