Winterize: Change oil, or just Drain Oil?

I like to do my oil changes in the spring time with fresh oil for the season, but I also want to drain the oil before winter so the acids don't stay in the engine all winter.

With that said, do I need to fill the engine with oil over the winter or can it stay dry and I just fill up with fresh oil in the spring?

The oil won't degrade by any significant amount as a result of the temperature or temperature changes. If you put in your new oil and filter you are safe for the spring. You are right to drain last season's oil rather than let it sit.
It can stay dry but there is no benefit, and there is a loss if the engine gets bumped over without oil.

You really need to do a complete oil change at winterization. You need to run the engine for a few minutes with the clean fresh oil to flush out the old from the bearings, rings, lifters, etc. Used oil is acidic, but it's the soft metals that are damaged the most, and simply draining the old oil leaves the used in these areas so you really aren't helping.

With an oil change in the fall, no need to do it again in the spring $.02

What oil do you reccomend I run in my mercruiser? Should I use specific QuickSilver or will any engine oil work? If so what viscosity is recomended?

Quicksilver or Mercury 24w-40. I do it before winterization, run the boat with new oil and fuel stabilizer before draining the cooling system.

I just run 5W-30 Mobile 1 or Royal Purple in my Mercruiser. Here's why you need to have everything done right now...next spring you'll run into some random 80 degree day and you don't wanna have to funk around with all that schitt. Just throw the battery back in and go!