I took the approach of starting with the Blue Hills rather than the Fells Skyline due to proximity to my home and because the Blue Hills Skyline route is much tougher.
Had light rain the first 45 minutes, so feet were soaked before even making it to the start of the main BH Skyline, and then rocks were a bit slippery, but made good time through Blue Hills, utilizing porta potty near ranger station.
Took a good 40 minutes at my car after doing the BH skyline out and back and the Burma Trail. Got some lunch (gluten-free pasta soaked in turmeric bone broth), dried off my feet and re-lubricated, changed clothes, and packed a new pack. Switched from road shoes to trail shoes for the remaining 40 miles.
Grabbed cold drinks and restroom break at Dunkin on the way through Hyde Park neighborhood. Also grabbed a drink from 7-11 in Medford after completing the Fells Skyline section. Roads were slower than expected due to waiting at crosswalks, but navigation wasn't particularly hard.
No injuries aside from a minor ankle roll on Fells Skyline that I recovered from quickly. Was careful to butt slide and crab walk strategically on the major descents at Blue Hills.
Finished about an hour after sunset.