Even with a trailer, it's always better to have 2 (capable) people while launching and recovering the TI. So if this fits your plans go get a DEMO!
I would measure the driveway/yard/garage first. It's a big craft. Don't bite off more than you can store.
Agree with both of these points.
I did forget to mention that with the TI there is a far greater chance that you will need a hernia operation or two if you are not very careful.
I know of 1, (seriously). Does yours make "2" mickey?
OK, now ya'll got me scared to go sailing! What are you guys doin with your Tandem Islands? I have a friend who solo launches his 24 foot Sea Ray with 2 bridges, a galley, a bathroom, and twin chevy automotive engines. Must weigh a couple of tons. Every time I go to the launch some guy or gal is launching a 400 or 600 pound wooden sail boat, or jet ski, or power boat with an outboard motor big enough to sink a TI and pin it to the bottom.
I've never had an AI, so I can't compare it to a TI. But when my back problems got bad I gave up car topping a 60 pound kayak and started trailering a 200 pound TI. So far my back is happy about the decision. Well -- that was not true for the first couple of weeks. I got the light weight Trail-X aluminum trailer and lifted the tongue to move it to the car and on to the hitch. In the water I lifted the bow onto the cradle. Then for the next month I used cold packs and pain killers and got no sympathy from my wife -- a normally kind compassionate nurse.
After recovery I made a firm decision that a TI is a big boat, not a kayak. Would have been the same decision for an AI. Thirty pounds of lifting is my comfortable limit. So I upgraded the trailer with a trailer jack, a winch (which I don't need most of the time -- but is super useful now and then), and a roller at the aft end of the tongue. I also got a trailer dolly for moving it around the yard and driveway. And I modified the trailer by putting the tongue under the frame box -- lowering the boat several inches so that it floats on easier. Again -- I would have done all that for either a TI or an AI.
Once I made the decision to launch from a boat ramp and store the vessel on a trailer, it matters little whether it weighs 100 pounds or 200 pounds -- or 600 for that matter. The only time I needed help at the boat ramp was taking out with a strong tideal current flowing past/over the ramp. Some one hanging out nearby took pity and cranked the winch while I stood next to the hull and aimed it parallel to the trailer. I think the situation would have been the same an AI.
I have similar needs to yours. I solo sail about 90% of the time. But the other 10% is very important. I love to share the ride with my wife, friends, and relatives. The second seat on a TI is wonderful. The boat sails great with either one or two people in it. I do find it a drag to pedal when the wind dies. I imagine the AI is easier. Plan to solve that problem with an electric motor and solar cell someday.
When talking about camping you say, " To lug a TI around on beaches is truly a pain." Do you mean hauling it all the way out and above high tide line? Or are you talking about bringing near to a good camp site? I hope to try camping with the TI sometime and I'm wondering how you do that. Beaches here are more like barnacle covered rocks than sand. Between the problem of sharp barnacles and the weight of either a TI, an AI, or a regular kayak -- beach dragging is not an option for me. I suspect I'd anchor out and use a long rope to tie off to a tree.
VaBeach1, good luck with your decision.