re: I See the Light

LBD it appears to me that your little red light wired to the utility is the solution to your irritation in having to run out to the outside power box. The only other option would be an automatic transfer switch, however it would only be "automatic" when switching back to utility, due to the 7 kW Dewalt not having automatic cranking & start, and the Dewalt would keep running anyway & need to be shutdown. In my humble opinion, your current setup is correct for your situation, thus avoiding the cost of an ATS and only operating it half the time.
UPS units are for short term use, like keeping sensitive electronics up during the time from utility drop until generator comes up & the ATS goes to generator. Batteries are not real efficient in storing power and require regular maintenance. 
It appears you've got the best solution for your needs already.