I have an 82 and 87 JS550. They dont have a ton of power either. You have to remember, chances are that this engine hasn't seen a rebuild. In 21 years things start to wear out. Also, 220lbs is a lot of weight to pull out of the water. I weight in at 160lbs and my 550 can do some stuff, but not like the new ones.
Having said that... it should get you out of the water and go. I would consider a top end rebuild and maybe a High Compression Head. You may also look at re-tuning the carb. If you want I can send you the page form the maintenance manual that gives you a step by step on how to properly tune the machines.
Your 440 should get up and go with you on it. It will take longer with you on it that someone my size, but it should still do it. Hop on youtube and tell me if it performs like the JS440 on there or worse or MUCH worse. I'll see what i can do to help. I love working on these things.
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