Scott -- You hit the nail square! I L O V E the back roads and H A T E the Interstates! And the thing that got me thinking about all of this "length" etc is the trip I took from Thunderhill track over to the Napa Valley.... Hwy 20 was exactly the kind of roads I love to travel on... a "stop and smell the roses" kind of life... and as you said - there were all kinds of "don't do this and don't do that and you can't go here" issues... and I "felt" big just dragging the trailer with my dually.
The washing and waxing thing -- I do with my cell phone.... as in "yo buddy -- come over and wash and wax my rig" so that's not an issue. And I want it in MY driveway so loading food - water - cars - etc is not a hassle. And in the end - I might reach the same conclusion you did... but I'm also not at all concerned about the total lack of resale. That just isn't an issue. The ISSUE is how I want to use it.... I'm trying to build in some freedom to roam... and bigger seems to take that out of the equation.
I also do not want to be hassled all the time with the issues you point out - over length - over weight - blah blah blah. So thanks for pointing that out.