1. All the good "everyday" ones are 3-seaters these days—race ones are two. The range is incredibly wide and dependent on your personal goals. I have a '20 Sea-Doo GTX and my wife has a '12 GTX. Both are awesome machines with great hulls (fun and stable), BUT mine has way better storage access—she is, as are many people, unable to reach her storage from the ski. So, at Braun Bay yesterday, she couldn't reach her anchors and ropes. Mine is directly accessible from my seat. I literally will not buy another machine without front access.
That being said: basic machine from 5-10 years-old: $7k, 1-5 years-old: $10k. Add two-three grand for better machines. These are "normal" prices, which seem to be returning here and there but aren't yet.
Single trailer: $800, double: $1200.
2. We have skis on our beach and, assuming no wave action, is fine (we're in a barely-ripple" area). Higher-end machines use fiberglass whereas lower-end machines have moved to plastic. The latter is better on shore.
3. Yes, but pretty cheap to have a shop do it as well. I pay ~$700 a year per machine for winterization, oil, new plugs, battery removal, storage, complete machine inspection, and spring wash.
4. The dealers I've spoken to aren't buying machines now because it's too expensive—people can get way more privately.
5. Were it me, I would look for two '20-'22 Sea-Doo GTX-170s with a galvi or aluminum trailer that someone bought thinking they'd use them and then ended up sitting. Under 100 hours with trailer would be ~$22-24k but you'd be getting machines with the latest features awesome storage access, and a super-efficient but plenty fast machine.
Alternatively, two slightly older GTI-130/155s with similar trailer. Those were pretty bulletproof everyday skis.
Feel free to ping me with more questions—as you know, I research stuff...a lot.
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