Welcome to the forum and congratulations on the new machine this year. To answer your first question, I would say most of us on this forum winterize our own machines and perform our own maintenance. If you have some tools and a decent mechanical know-how these engines are really pretty simple to work on, winterization included. Since it sounds like you are new to these machines, I would go ahead and download a copy of the service/shop manual for your ski/engine. You can do this by clicking the link at the top "manuals", there are plenty of service manuals that you can save as a PDF. It's a good thing to read through the manual once to get an idea how the engine works and how to perform maintenance tasks when you're new to the game, helped me a bunch when I first started.
Next, do a search for "winterization" on this forum and you'll find countless threads on the subject. Below are a few that I found quickly, but many others out there to read:
http://www.seadooforum.com/showthread.php?55224-Winterizing-a-boat&highlight=winterization
http://www.seadooforum.com/showthread.php?54401-Pumping-antifreeze-speedster-winterization&highlight=winterization
For your specific questions:
1. Storing with fresh engine oil is kind of under debate in most arenas. As I understand it the reason to store with fresh oil is b/c used oil contains chemicals from combustion that can be corrosive. Really dirty oil sitting in an engine for long periods can deteriorate the internal parts and seals. If it were really dirty I would change it at end of season, but with only 10-15 hrs of use I usually just leave my old oil in until spring time and change it at the beginning of the season. Lots of debate on this and I'm sure some would disagree with me on this topic. It's really up to you, but make sure to also change the filter, its a very simple project to do with the right tools.
2. This is another topic of debate in most circles, I prefer to run the tank down as close to empty as possible, add stabil to the gas tank and run the boat around the lake a couple times to get the stabil into the fuel system. I then fill the tank with fresh gas at the beginning of the season. The manufactures of the gas stabilizer tell you to fill the tank, but it's probably b/c they want to sell you more of their product to treat the 25 gallons...
3. Very important to get the water out of the engine. Your engine (and mine) are supposed to be self draining, but I don't trust that. I pump rv antifreeze into the flush port (with engine running ofcourse) until it comes out the exhaust pink. Then I know the system has be treated and will not freeze. Seadoo recently came out with a new procedure to blow out then engine with compressed air which apparently does the same thing, but I feel safer with the antifreeze method.
4. Main things are to treat the gas, get water out of engine, and lubricate everything with a water repellant spray such as wd-40. There are a few more other minor things to consider, but I will point you to some of the other threads which have already gone over the full process in detail. The shop manuals also have a section about winterization that is very detailed, so have a read and post back if you have any other specific questions.
Good luck!