Let's say I want to throw money...

In the water and buy an older ski/speed boat.

What should I look for and avoid? 

Personally, I shy away from old inboard/outboard boats. I think outboard is much easier to deal with swapping or repairing. Also higher power to weight ratio. Compression checks and general maintenance checks on any motor.

Other than that the main problems are soft floors and transom. Most of them were left outside and the wood floors and transom (and probably stringers) are rotten by now. They can be replaced but it's a huge, PITA job. 

Why older? So you can spend more time and money on fixing it, and less using it?

I hate to be sarcastic, but I've had a tendency to repeat this mistake, only with fishing boats instead. No such thing as a cheap boat.

I've gotten a lot more use out of my miatas than any of my boats.

Try standing in the shower while tearing up twenty dollar bills. Same effect, only cheaper.

What is your budget, specific use (pleasure boating, tubing, skiing, fishing, cruising), and what water will you be on? Will you be towing it every time you launch? How many people will be in it when it’s used on an average trip?

Where will it be stored—indoors or outdoors?

This.

Donzi Sweet 16

In reply to Grtechguy :

Aren't ski boats and speed boats very different things?

Around the mid 90s a lot of ski boats became wood free.  That is what I would look for.  They are pretty simple a car engine and a hydraulic transmission.  I had a 1985 century tournament skier for a long time that pilot Braden has now.  It had rotten stringer that I replaced and would not do that again.  Mine had a 454 which did nothing more than use more gas.  They are a lot of fun for inland lakes in Michigan.  Rough water not so much.

NOHOME said:

This.

Donzi Sweet 16

Donzi was my first thought. 

Duke said:

NOHOME said:

This.

Donzi Sweet 16

Donzi was my first thought. 

What these guys said.  It won't be cheap to buy or run, but it will still have value when you get tired of it. Also one of the prettiest little fast boats you can get, and that has to count for something.

ultraclyde said:

Personally, I shy away from old inboard/outboard boats. I think outboard is much easier to deal with swapping or repairing. Also higher power to weight ratio. Compression checks and general maintenance checks on any motor.

I'll offer a different opinion here.  I have owned plenty of both and my last two have been I/Os.  The first was a Baja with a V6, and with next to zero parts purchasing, a nicely-built 383 went in its place.  Current boat has the 3.0L 4-cylinder which is slow, but as reliable as dirt.  If I want to swap to a V6 or a V8, the parts swapping is remarkably simple.  The V8 would need different ratios in the outdrive, but I've had them apart so many times it is an afternoon job for me.

Outboards do give the most power/weight, and if your main goal is speed, do it.  Outboards are stoopid expensive, though.  I just sold a 1992 Mercury 25hp for $900, but the 3.0L in my I/O could be replaced with a $250 junkyard motor and $100 worth of gaskets and a carb rebuild kit.

The main misconceptions about I/O motors that usually keep people away are:

1. Marine I/O motors are reverse rotation and parts are expensive.  The fact is, almost zero marine engines are reverse rotation since 1974.  Someone got the brilliant idea that, instead of swapping 30 custom expensive parts inside the motor to make it work backwards, we can change the ring and pinion in the outdrive, vee drive, or velvet drive for $40.  Even in dual motor applications, both motors spin the same way, but the gears in the outdrive just spin the prop shaft opposite of each other.
2. Marine motors have expensive forged crankshafts and pistons to handle the stress.  That was true in 1960.  Modern hypereutectic cast pistons and cast crankshafts put many of the old forged cranks and pistons to shame.  The 383 in my Baja was built with a bone-stock vortec block, a cast crankshaft, hyp pistons, and truck heads.  It took 6000 rpms all day.
3. Marine parts are super expensive.  Yes. They are.... if you buy marine parts.  The main things that are marine about them are the spark-supressed electronics; dizzy, starter, alternator.  If you look at them, you know what's different?  There are screens over the open ends.  Marine alternator dead?  Go buy a $25 reman from a 65 Buick and swap the little screens over, or for that matter, just put the guts of the new one in your old case.

I/Os are heavy, though.  Dry weight on my 18' bowrider is 2100 lbs.

For a fun, stable, fast boat, look for an 80s Baja 190 sunsport.  Shallow vee, probably came with a V8, give it 300 hp and expect 60 mph.  For way more speed, look for any Hydrostream tunnel.  Still stable, but with a 275hp outboard you could pretty easily hit 80 mph.  More later... gotta hit the road before the flash flood warning sweeps me away. :)

mtn said:

What is your budget, specific use (pleasure boating, tubing, skiing, fishing, cruising), and what water will you be on? Will you be towing it every time you launch? How many people will be in it when it’s used on an average trip?

And how often would you actually use it. My boss has a super nice pontoon boat, both vehicles can comfortably tow it. He said they use it less 6 times per year because it's a pain to hook up, unload, park vehicle, etc.

Floating Doc said:

Why older

Let's say under $5k,  seats 5 and can pull a wakeboard or tube.     Quick enough to be fun.

Yes, I will be towing with an F150.     A shallow draft would be preferred as closest water the Grand River.

In reply to Grtechguy :

The best way to enjoy a boat as you described, is to rent one. It's expensive per use, but is by FAR cheaper and less headaches.

Grtechguy said:

Floating Doc said:

Why older

 

Let's say under $5k,  seats 5 and can pull a wakeboard or tube.     Quick enough to be fun.

Yes, I will be towing with an F150.     A shallow draft would be preferred as closest water the Grand River.

You will want a 18-23 ft runabout bowrider. I/O’s are likely cheaper than outboards. Wakeboard will probably need more power than a tube. On smaller water like a river, you can get away with a lesser built boat like a bayliner, but for you, I’d be keeping a search out for Sea Ray, Rinker, Chaparell (probably well out of your price range), Cobalt (same), 4winns, or similar. 

If you go outboard, I’ve personally had a LOT of experience with Merc’s and OMC’s. I’d hold out for a Yamaha.

I am selling this boat for my FIL. It would be a pain for you only because the trailer is a pain, it should be replaced with a trailer meant for this size boat, but it would be about the boat you’re looking for. 

https://up.craigslist.org/boa/d/marinette-1998-rinker-captiva-212/6927212182.html

as I am a sailor, my idea on speed is biased.. but I have spent enough time on speed boats to know that 40 mph feels damn fast, especially when the wind is making your eyes water and your hair is being pulled back. Unlike a car, which has suspension, boats work on their hull shape to cushion the ride. 10 mph can have your pounding badly on a rough day.

In reply to mad_machine :

Amen...

Worked at a shop that did fast and offshore race boats. Been over 100 mph on an Alison bass boat and a Skater offshore cat plus a few others that only made it into the 90 mph club.

I hate boats that go over 50 mph. Scare the E36 M3 out of me.