David,
Sounds like much of the story is getting repeated by now, but let me see if I can address some of the questions you asked.
Our first TM was a 1995 3326 King. We bought it in 1997, and sold it in 2012. We now have a 2007 3124KS. I agree with other posts that you should look at the 3124KB. Having TM build you a 3326 would probably be very pricey. TMs are very easy to tow. This aspect is not hype. The one unit that we've heard about on this forum that may be prone to sway is the "new" 2922, which is apparently rectified with an anti-sway WDH.
I would agree with you that new TM's will depreciate faster than new Airstreams. I also agree with a previous post, "apples to oranges."
Unquestionably, the most verbiage in this entire forum concerns the toilet. We have had no issues with the Electramagic recirculating toilets in either of our TM's, and would never consider replacing them with a cassette. Others complain about smell (easily mitigated) and flushing issues (also easily mitigated), and the thought of "what's recirculating" (can't do anything about that). At the end of the day, I think which direction you go on this is a personal choice, driven mostly by the type of camping you do. If you dry camp a lot, a cassette makes sense. If you camp with sewer hookups a lot, it doesn't.
I've already answered the question about how long we've owned a single TM (almost 16 years). From my perspective, the only "must" option is air conditioning (I live in Texas). All the others have to fit your own personal desires. I can't answer the question on kayaks, but if you join the forum, you will be able to search on this. I'm sure somebody's found a solution!
Good luck with whatever decision you make,
Dave
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