Re: Swapping out a 305 for a 383.
QC brings up a good point in that you really have to think and feel this through from a variety of angles.
What might be important as a consideration to us might not be to you, and vice versa. Some things that might be considered (even if only in passing):
-Fuel (There are a bunch of boats where I dock that aren't run more than few times a year because the owner can't afford to, but didn't know that at the time of purchase. Gas prices are volatile; you might have to hedge).
-Resale (This repower might leave you upside-down. If so, how far upside-down are you willing to go? That's between you and the Financial Department; start bribing early, do so often.)
-Cash flow (Liberal application of bribery often yeilds desired results. For what it's worth, avoid using analogies involving shoes that aren't worn or purses with tags still on them when the phrase "wasting money" is used to thwart progress. But, it's typically less costly to do it right the first time than it is to do it twice. And it may be that all of the viable options mean you seriously have to consider getting a completely different boat and parting out or selling what you have. There are still a bunch of great deals out there.)
-Length of season (At least for me, it was hard to justify certain options given our five month long boating season. YMMV.)
-Power (It's easier to run at 3/4 throttle than it is to run at 8/4 throttle. If it's there, you can control how much you use; if it's not there, it ain't there. You've giving it all she's got.)
-Desire (The emotional aspect of the whole deal. You want the XYZ because you want the XYZ and won't be convinced otherwise, like the package it comes in, the stickers, it being a turn-key, the boat deserves it, it'll help you sleep better at night, it's got safety features and since she goes out by herself her safety is top priority, or whatever.)
-Ability (If you decide you want to try your hand at building all or part of the engine. Depending on what you think of your mechanical abilities/desire to learn, and what she thinks of them, be prepared to offer a clever response if safety comes up.)
-Warranty (There something to be said about knowing it's right because you did it and went the extra mile to make sure it's right. There's also something to be said about dealing locally with someone who has a reputation for standing behind their work; they might have a bad day and it happens to everybody, but it's typically easier to make it right when you can do a face-to-face. Even still, there's something to be said about a warranty book with impressive looking terms from a big corporation. Just be sure to read the fine print on limited liability contracts since there are places out there offering contracts with no questions asked.)