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Once again, thanks for all your input. I think I'll steer clear of the 2720 until I get a heartier vehicle to tackle my area's steep inclines and oxygen deprived air.
I have seen the trail-mini, however it won't work for my situation since I need more sleeping space.
The Chalet has a model with bunkbeds that sleeps 4 and weighs less than 2000lbs. Maybe I'll check that out...
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We also looked at the Chalet XL 1920 as our TV is a 2008 Dodge Grand Caravan. We ended up with a used 2619. I really like the Chalet, but the biggest issue for us was cost. You basically have to get a new Chalet to get what you want, whereas you can get a several year old TM for significantly less. The price difference between the two would just about allow me to upgrade my car to a better TV (I say my car b/c my DW would not give up the Caravan).
I really went back and forth, but after reading a lot of posts here about towing, I decided to learn all I could about weights and make an educated decision. I weighed our Caravan loaded up for a two week trip to visit the in-laws, took into account the GVWR and all the other weight ratings and found that I had some room to spare (still had 3700 lbs of towing capacity). But the Caravan is different than the Sienna in that it as a 3800 lb tow rating (allowing for two adults and their stuff - whatever that means) and a higher GVWR than the Sienna.
My advice is to do the math and see if it's possible to tow it safely. Even if it is, that doesn't mean you'll be comfortable with it, and thus it wouldn't really be safe. If it isn't, look for a Chalet, but consider the price difference. If you were wanting new anyway, then the Chalet would be a great option. The RPod by Forest River is another good option, though it would introduce wind resistance and lessen your gas mileage. But a new one can be had for around $11K - much cheaper than a Chalet.
Sorry for the long post, but your situation is exactly what we went through. I figured if the numbers worked out, then it was worth a shot (but make SURE the numbers are real life numbers). I may be back here in a couple of months looking to upgrade the TV though.