For a trouble free (relatively) season, the boat should be gone through and all the maintenance done.
I'd want to pull off the drive, check the bellows. gimble bearing and ujoints, and lube the gimble, ujoints and driveshaft splines. Check the gear oil in the drive for water (remove the drain plug briefly and see if water comes out first, or if the oil that comes out is milky colored, if so it needs to be pressure checked and re-sealed.
Once you get the drive back on, I'd replace the raw water impeller and look at the thermostat (check it in boiling water to see if it opens at the usual 160*) and cooling system hoses (check for condition and good clamps). After doing that, I'd take a look at the sparkplugs and replace if needed, same with the dist cap and rotor. I'd also remove the fuel filter and pour out the gas that was in there and let it sit in a glass jar, and look for water on the bottom, if not, then put on a new filter. If you found water I'd have the gas tank cleaned. Then you can start it up on the water muffs, make sure the impeller is sucking water and water is coming out the transom mount exhaust area. Look to see if oil press, volts and water temp are normal. Also look at the hoses for leaks, and the sides of the engine and heads for any water leaks that could indicate leaky freeze plugs that need replacing...
After you warm it up, you can check compression. I don't know the exact specs for the Ford 5.8 but they should be from 130-175 or so for most engines. If you have a low one it may be an exhaust valve with a rusty stem that is getting sticky. Finally look at the joint between the risers and manifolds, if you see rust tracks, then the risers should be removed and the gaskets replaced (very important to inspect the area where the gasket seals, if that is corroded they might not seal and then you can get water down in the cylinder when you shut off the engine (which rusts exhaust valves). If there is much corrosion the manifolds and risers may need to be replaced.
When it's running on the water muffs, with the prop removed, make sure it shifts into fwd, neutral and rev like it should. You don't want to find out it won't go into neutral or rev when you are heading toward the dock (like my Cobra did when I first had it, fixed that real fast!).....
After running it on the water hose, I'd change the motor oil, filter and the gear oil in the drive.....I do this every year at winterization and if I use the boat a alot, I do one motor oil change in the middle of the season...
Also look at the anodes on the drive and transom shield, replace if more than 1/2 deteriorated....
I know this sounds like a lot.... but.....keep in mind that this boat is going on 16 years old so there are a lot of things that should be checked for a trouble free season. I do all of this to our old boat (some during winterizing, some in spring) every year and that's what kept it reliable for this long...
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