Im sure you could find some reason why any solution has its pitfalls. Everything is dangerous in the hands of the unwise!
I would have to think any generator built since...nineteen-o-shit would have its own breaker. If not, install a breaker in line to the outlet.
That being said, my advice on using the plugin method would be, don't run a huge generator this way! Keeping in mind that the outlet I use is a 4 wire, (one grounds the generator), 50 amp circuit, don't try to run everything in the house. Aside from the the breaker not doing anything, the wiring wont stand a 100 amp load very long either, I would suspect. This system is emergency power only.
Doing the math, and allowing some safety margin, I can run my heat pump, refrigerator, a couple of lights, and a television. When I need water, I turn off the heat pump and run the well pump, then switch em back again. I have always checked the wires for heat, (I was leery of doing this myself, for a long time) and have never even found the slightest bit of warmth in the wiring. (BTW...one thing that noticeably draws the generator down? A 110v hair dryer! BIG amp draw!)
If you want a full power generating system, so life can go on without any inconvenience, by all means get a big enuff generator, and have it professionally installed, with all the automatic toys!!