There is definitely a difference between the 15 2-stroke and 15hp 4-stroke. The 4-stroke is not going to have nearly enough power at low rpm to get you on plane with a big load so that the motor would finally get up enough rpm's to actually make it's full 15hp. I would compare the 15 4-stroke as far as planing power to a 10hp 2-stroke, or worse. I'm sure that some will disagree, but that's my experience with them. I did once own a nice lightly used 15hp 4-stroke Mercury and although it ran smoothly and quietly, it didn't have nearly the power that I was accustomed to with a 2-stroke 15hp. I only kept it for about 2 weeks and sold it.
A '53 15hp Superfastwin is relatively speaking, quite a powerful motor, and one of the faster. 15hp OMC's made. If it has been properly tuned with good compression and new ignition, it is very reliable. You are not going to find a 15hp 2-stroke or 4-stroke that will outperform the '53 15hp if they are all in good running condition.
From my experience, a 550 pound load on a lightweight 14'36" jonboat with a 15hp 2-stroke would have a hard time getting on plane, and max out about 19 or 20mph at best. My 2-stroke 15hp outboards go about 22mph on my boat (15'42" duracraft johnboat) with just me and a 6gal. tank of fuel.
Basically, I would check the compression on the '53 model and if it has around 105psi and both cylinders are within about 5psi of each other, I'd clean the carbs, replace the coils, plug wires, condensers, points, fuel lines, water pump impeller, and use it. If the lower unit leaks, it's about a $40 repair if you do it yourself. You might even add a fuel pump and use a single line modern tank for about $40, or install a pressure tank rebuild kit for about $30. If your motor has good compression and a good set of gears and clutch dog, fixing it correctly yourself would be the best and cheapest route to go if you want a 15hp motor.
Just an idea,
JBJ