I don't know that you're over analyzing, but I do think that that performance of portable amps is overstated/exaggerated a fair bit. Even though I own a portable amp (a Mister X PINT), I do feel that if the situation allows then unless the majority of your time is "on the go" and you feel that that is a desirable scenario, then a stationary solution is better. That being said, the only scenario that I'd see mucking that up is if you can only spend 1001-150 max, which IMO the only viable solutions are portable, unless you can somehow score a dynalo or something of that sort.
But yes I don't really place much value into the whole X portable amp can compare with home amps, especially ones that are priced a fair bit higher. However, overall I do feel that certain portable amps/designs are ones worthy of looking at. But no I don't see a point in investing that much serious coin in a portable rig/