It is easy to trailer (you will not even know it is behind the car or truck).
Isn't that ever the case! Just don't back up suddenly, having forgotten you have a trailer in the back!
Medium size lakes sounds about right for a DS. Just checked out the Wikipedia for Green Lake in Wis. (not a namesake). From what I read, that would seem a great lake for the DS.
I've sailed on lakes that size. They're big enough so you don't get to visit every single corner each time you sail on them, and yet not so big that you get big waves or even swell.
One Lake I didn't enjoy with the DS was surrounded by hills/mountains in a way that made the winds very erratic. Having to deal with very sudden and strong wind-shifts is not the way you'll have fun in a DS - esp. if you have a non-sailor with you.
Mind you, the DS handled the gusts quite well, by first heeling, then rounding up, somewhat like twisting out from under the wind. Worked every time and I never got close to capsizing. However, it's not the kind of thing I want to put "passengers" through, so I now stay away from high shores and the eddies they bring with them.
I've limited myself to day cruises - sometimes they go into the night (I
love night sailing under the right conditions), but they don't involve overnight stays.
That said, I can see how the DS would be great to take a moderate supply of camping gear with, to stay overnight on shore somewhere. But those who sleep on a DS must be the kind of person who would think nothing of bivouacking in a bag suspended half way up a mountain.
Doable, but a bit hard core, in my view.
I've taken many people over the years, most of them not experienced sailors. The DS responds more deliberate and more forgiving than other boats I have been on, which makes it a lot easier on newbie crew. In most conditions, it can be sailed dry.
The boom is high on a DS, so you don't need to crouch during tacks and an unexpected gybe will not threaten seated crew or passengers. You do need to shift weight, but many non-sailor friends are happy to volunteer as "live ballast" in exchange for a cruise.
If you plan on cruising, have a reef put in the main and add a reef hook or single line reefing (if you've followed the forum, you know where we discussed these in the past). Being able to depower will keep your crew happy.
So, unless you have some additional concerns that you didn't mention, I see no reason why you couldn't be happy with a DS.