Truth is I dont think this boat is worth my time or money but I appreciate the wake-up call about cheap vs new boats.
I've bought a couple of cheap rotten boats (that I knew were rotten when I bought them). One of them is ready to go back in the water - once it warms up a bit, but it took me a year of working on it in my spare time. Total cost (in materials) was far less than I would have spent on a new boat, and I KNOW it's solid. I replaced every scrap of rotten wood in that boat! I just don't have the finances to buy a new boat.
The debate I have is if I can only afford to buy used boats but they are likely to need repairs too, then what do I look for?
Look for a boat that you like - that you will like to have for a long time. Preferably with a solid trailer included. Buying a trailer separately will cost more than buying a trailer that already has a rotten boat on it. Make sure the boat is more or less mechanically complete. In other words, steering works, all gauges are there, trim is somewhat functional. If it's an outboard. make sure it runs, gearcase works, and it's something you can still get parts for. If an I/O, make sure it's a Mercruiser or Volvo/Penta (avoid OMC because of parts availability). Make sure the block isn't cracked due to lack of winterization, etc... You know the mechanical systems will need maintenance, repairs, etc. but that's still cheaper/easier than having to find one separately. Make sure windshield and frames are all complete and in good condition - so you're not having to scrounge for oddball "hard to find" parts. Also make sure to budget/plan to spend a few thousand in materials to make it "new". And take your time doing it properly.
Also, the old Chrysler 70 motor works good but lacks “modern” amenities like trim and tilt, is it worth putting on a new hull?
I certainly wouldn't go buy one of those Chryslers, but if it runs well, you already own it, why not put it on another project boat until you find something newer to bolt on there? This is a viable alternative to my earlier comment - if you find a good hull/trailer, fix up the hull, and bolt the motor you already have on it to get on the water.