Billy, I totally agree with your sentiments.
I have often thought about getting some big Dob or other big scope. But carrying out (by pieces, even!) my 8" SkyView Pro GEM system is enough for me. Any heavier, I probably would lose interest in stargazing. In fact even as it is, this summer, carrying out the mount with tripod attached, somehow, one of the legs caught the turf, tore out a divot, and sent me falling, almost on top of the mount. Of course, it... and I... fell onto the paved path, not the grass. I got a scabbed over bruise on my shin for several days and my spreader was bent (restraightened amateurishly with a pair of pliers). What's it going to be like in ten years, or even five?
Yeah, after that, I was a lot more careful, making sure no tripod leg tips the soil, especially when my pant leg rubbed against the scab over the bruise.
I suppose, get as much scope as you can handle without emotional resistance when you think of taking the scope outside. Of course, each of our circumstances vary: I am in suburban New York, and even there, there's more concrete than air molecules over the same area; someone else may be by the drier and more open-air and lower-crime states and so may be able to either keep their scopes mounted outside or have the space and wherewithal to make it more easily mobile. Therefore, this guy may be able to handle more scope (a.k.a mass, or, weight) than a city boy (I suspect elevators and stairs are not very friendly to telescope transportation).
If you don't in the end want to take your scope outside, it won't matter how big or how good it is!