Man you guys are just asking for trouble Trying to tow 29 with anything less than a 2500.
It will just KILL your veh. I am not even guessing about the law.

Get a 2500 or 3500 SRW and the 33 and be Happy for Several yrs!! 29 just gonna make you want more in 3 yrs if you are just steping up from 25

Also if you have had the Alum platform you cant go backwards to the 302. Way to small an area to swim off of.
As for 500 HPs, top ends are easy as long as you do it BEFORE it blows

Just my 2 cents

What is actually involved ina top end refresh?

IDK why people say that. I have a 280, it's every bit as big as a 302. Probably is heavier as it's and older boat. I pull it with a 1500 Avalanch that has close to 200K on it, and have never had a problem with it pulling that boat. Boat does not push the truck around, and has no problem getting it out of a ramp.

Would not try to pull a 33 with it, but it has no problems pulling my boat.

My 29 and 30 Bajas were marina kept with in and out service. I towed occasionally. Should have mentioned that. But if I were in the market for a 29OL, I would tow with the Expedition without concern. Would fit MY needs just fine. I tow from winter storage to marina in the spring and fall plus up and down the ramp. I wouldn't maintain another vehicle for that. In fact I'm ready to get rid of the 342 because my truck pisses me off.

A 29 or 30 will drag a 1/2 ton down a steep ramp if you're not careful though. Going electric is the best towing upgrade I've ever done.

I tow my 302 with an 07 Chev 1500 4 door. No issues

Have you weighed your 302? I don't think I will have a problem with the expedition. Its rated for 9200. It actually pulled my 25 better than my f150 fx4 screw. More weigh in the rear I guess and my truck was only rated for 8500. Probably b/c of extra weight of 4x4.
You could feel it behind the truck but not the expedition.

Never weighed it. Truck is good for 9400.

I stopped at a cat scale on the way home with my rig.

2500 gmc crew cab, and baja 342 boss, and trailer.

Truck was 8,680 (2 of us in it), trailer and boat was 10,680 LBS

19,360 lbs rolling down the highway. and the boat was pretty empty.

The biggest problem is not if the truck will pull the weight but is what the truck is rated for. If God forbid you are in a crash with truck and boat and it is over weight any at all the insurance will give you a fit. You can bet if you have a wreck with a boat that size pulling it with a 1500 or similar the insurance company will weigh the boat. Over the dry weight of the boat you need to figure around 3,000# minimum to cover trailer, fuel and all the junk associated with a trip to the lake. 150 gallons of fuels is around 1,200# by itself. IMO a 29-33 foot boat should not be pulled with no less than a 2500 or 250. Our 33 on the trailer with a full load of fuel and all the junk for a trip to the lake is 12,350#.

OK, I'm officially calling BS on this thread....friends actually PITCHING IN for gas??? Hell, It's taken me years to train mine just to bring their own damn beer...Maybe I need new friends...

On the towing issue, I would definitely look for a 3/4 ton. I had a 252 that I towed in Austin with a 4 door Tahoe. it was sketchy at best. I ended up finally shelling the tranny, and stopping was ok, if you planned ahead. I went up to an F-250, and you couldn't even tell it was back there. I have recently moved up to a 32 Fountain, and I think it is lighter than the 302, it still towed like a dream. I just got a Chevy Duramax, and haven't gotten the chance to tow with it yet, but I'm sure it'll be the same. If funds allow, and you are looking for just a tow vehicle that you won't use all the time, I would say look for a F-250 with the 6.0 diesel. They have lots of (fixable) problems, so plan on an additional 3k or so on top of the purchase price if you do the wrenching yourself. They can be made into very reliable motors with some elbow grease, and I would have kept mine if it was not my daily driver. All that being said, you can pick one up dirt cheap because of their reputation, fix the know issues, and drive it till the wheels fall off. Also, the older 5.9 dodges are good trucks, they just have a tendency to eat trannys when towing heavy. They can be found pretty reasonable too. I would definitely suggest going with a diesel with as heavy as you're going to be towing. Yes, fuel is more expensive, but it will still get better mileage under load than a gas motor. And last a lot longer.