// random brain dump = on
Excellent replies! I wouldn't say that I'm hugely experienced with aluminum boats, grew up on Fiberglass, but here's what I noticed. That boat looks like it might have been stored under a carport or maybe covered at some point - I only see a few acorns in it. Down here, it would be full of acorns if it were just sitting out. I also don't see any waterline inside the boat from where junk clogs up the drain and fills up the boat. The dirt on the tires and seat puddles from rain say it's been sitting out lately.
I always hate seeing where a boat sat with water in it and potentially froze with water in it (water expanding into ice breaks things) but it does at least prove the boat was floatable... if it will hold water in it for any period of time, it should keep water out when it's on the water for a reasonable time. If it lived a covered life, it was probably better taken care of. The keel looks pretty good from the pics. I usually look to see if it's straight and not pounded flat from rough landings and misuse. That is kind of an indicator to me of how it's life was led. I would crawl under it and look for missing rivets and great long scratches / bends too.
The trailer shows signs of newer winch and / or strap and the wheeled jack and lights look newer too. I can see where it started to get power washed and then stopped - maybe somebody got bored with it and bought a new boat. The back story should be worth hearing. See if the carpet is peeling off the bunks or the bunks are disintegrating. I think I see trailer buddy bearings, you can get a bit of a clue if they are really recessed like it hasn't been greased in a while. They will be flush with the bearing cap when they are full, another sign of maintenance that is iffy. If the grease is brand new it says either putting lipstick on the pig or they took reasonable care of the boat. Recessed and black grease says lack of the same.
A 5.5 would likely not plane it even with zero load and maybe 11 or 12mph if it could plane it... you'd be sitting in the middle of the boat to get it to plane I bet. A modern 4 stroke 9.9 can be parts changed over to a 20 (!!!) a lot of times but costs 3x what the boat costs. I have been looking at the Tohatsu/Mercury models that use the same shortblock, pretty much the same engine with different fuel delivery. The cost to convert a 9.9 to a 20 on those motors is, not ironically, about the same as the original price difference and a warranty violation. The tag on the boat you are looking at would give you a model number and HP rating, which I suspect is 25-40hp. I am on the fence these days. I don't want a 50 pound toolbox to be required equipment for a fishing trip and the latest four strokes are not all that much heavier than their two stroke older brothers. Before I lost my train of thought there, a modern 9.9 four stroke is a big cubic inch motor that you can grow into much more if you get terribly bored with it (and have the wallet for it).
I'm in Texas and they are probably some of the most picky when it comes to small easily stolen watercraft titles. 500.00 fine for not having your boating card with you in a boat you are operating. They don't mess around. Texas has a web site where you can run the boat numbers for ownership. There are two places the titles must be signed, front and back. Make sure your paperwork is done according to your state. Sellers here frequently fail to realize it has to be signed in two places, and sellers are notorious for buying it, never transferring it into their name, and then selling it when the registration goes out. THEN you find out they never transferred it because the title was only signed on the front. Then you find out the original owner passed and Texas wants their tax money - they require it to be registered to every owner - so that gets messy. If there was a bill of sale with a really old title, it makes it even more fun. The newer titles include a bill of sale / assignment on the back. A trip to the parks and wildlife (where our titles get transferred, your organization may be different) to ask them exactly what it takes may be time well spent. The website here is pretty good, but the nice people behind the counter can give you the skinny and show you where most people fail. This is the longest paragraph because this is the ugliest part of boating down here.
The trailer tags show Maine, and I think they use MOSES for registration, you might be able to get some history / information from here:
https://www.maine.gov/ifw/about/commissioners-office/licensing-registration.html
Back to the boat, I think that may be an F7 or maybe an FD, probably 60's era from the stickers. I would take measurements from the boat and compare to the brochure to be sure, but it looks like an F7 or FD... either would handle a lot more HP than a 9.9, the FD holding much more than an F7. Try this brochure for a starter?
https://catalogues.brp.com/aluma-my67-catalog-enus.html
The last thing I would say is a 14 foot boat looks easier to handle by yourself. I fell into that thinking and then the wind came up and I was re-thinking a 16' boat. At my age, I'm starting to think any new to me boat will come with a 20" transom, more freeboard, and more motor. It's not to brag about how fast it is but I'd rather head to shore with a 30mph capable rig than a 13mph rig when a little squall blows up. I had a buddy who liked to take risks when he was in his 20's. Tied a milkjug to a 100ft line to the boat so he could find it later when it turned into a submarine. I do _NOT_ share that thinking.
All of that blathering out of the way, looks like it could be a neat boat! I would have no problems running a 20 on it personally whether it's a hotrodded 9.9 or whatever. If it's an FD it was tagged for double that. A good running 25hp JohnnyRude would probably make it quite sporty! The thing to keep in mind for me is - would I send my kid out in it alone? If you are thinking older good running two stroke, I'd guess a good running 9.9 would be okay with a light load and one person, if that is the lake limit. I'd be one of those guys putting 9.9 stickers on the cowl of a 15hp two stroke since they are mostly identical and visually the same. I don't run my stuff wide open all the time any way, but when I want it to run hard, I want it to be able to. The lakes I go on aren't HP limited but the newer four stroke 9.9 -> 20 conversions would have my attention if I did.
The pricing is not too far out of line with the last year or so's junk down here... if the boat was taken care of, I'd think it was worth it. Some guys (like me) will stop talking to you immediately if you low ball them on an OBO sale. A 500 dollar offer would piss me off and I would say "Good day." I wouldn't be insulted with a 900 dollar offer, but probably wouldn't take it. Come January 31 with outrageous property taxes due, I might consider it. YMMV...
OH - I forgot. When you look at all of these things and think "I can do this and I can do that" keep your available time in mind and consider whether it's worth more to start out with something to go fish or play on the water without having to work on it, or whether you want to walk by it and throw 100 bills at it all summer. For me it's really easy to bench build these things from a keyboard, and I like working on them but there are times where I just want to fill it with fuel and go and not have to worry about it. Good luck with your boat hunting!
// random brain dump = off