If you fix the boat it will buy you the time to upgrade to exactly what you really want at the price you can afford, and will be worth more when you sell or trade it in.
2ft does make a huge difference and 3.5ft even more. When I went from a 16ft skeeter to an 18ft Stratos it was amazing. I thought about repowering it but I really wanted more fuel capacity as 24gal didn't go far enough on Powell even when dangling rope working. So I upgraded to a 21.5ft triton and wow what a difference that made over the Stratos.
In the end you only live once and who knows how long that will be. Only you can decide what you want and can afford. Best of luck on your decision.
agree with Meatwagon -- fix up current and start looking for replacement.
For me a replacement would start with a older boat ( 10+ years) that current owner has repowered to a 4 stroke-- lots of buyers are just looking for a "new" boat, and skip right over the older that has a new repower. -- my last 2 boats have been this way -- current has a 2018 Honda 250 -- cost for whole set up was about the cost of the engine put on boat 3 years before I purchased.
For the cost I would definitely fix it, after that go with your gut. I sure don’t regret upgrading when I did which was perfect timing. I couldn’t do what I did at current prices. Good luck with what ever you decide! Just get it done and start enjoying it, time is shorter than you think!
Hey sorry to hear about your situation. I think you actually reached out to me earlier this spring and was wondering if I knew of anything since I kind of dabble in buying and selling them. I was going to say exactly what meatwagon and Davew said, phone it in, get it fixed with the current motor, use it as is, and actively search for another one. It's not worth nearly as much to somebody with it needing repairs as it is ready to go. If you can float the money for another boat without selling this one look for something this coming off season and hold on to yours until about March or April and then list It. Mine's a 22 ft I wish it was a 24 LOL! Except when I have to park it in my driveway or wash and wax it as previously stated.
I'm in the "get a whole new rig" category, too. First, your engine is old and the company that made it is out of business. You don't know how long parts will be available. Second, most boats today are sold as boat/motor/misc. equipment packages and getting just an outboard for re-powering is actually pretty tough right now. Even if you can re-power, it will cost a lot. Larger outboards are crazy expensive, and then you'll have to purchase all new controls and have them installed. You might also have to change out your steering linkage, too. When you look at all those costs vs. the cost of a completely new rig minus what you might get for your current boat it might not be that much more just to go with the whole new rig.
You'll love the new 4-strokes. They are now as light as what comparable DFI 2-strokes used to be. They have far better acceleration and top-end performance than the 4-strokes of old. They get great gas mileage, and I'd doubt you'd ever wear one out unless you run it hard 5 or more days a week every week. Four-stroke car engines can go 200,000 plus miles now pretty regularly, and 4-stroke outboards will go a long ways, too.