Congratulations on such a significant weight loss! That has got to feel great.
For your foot that flares out, clipless pedals can be set-up from the start at whatever cleat position you consider “neutral”. If you want to nudge it back toward being in line you could rotate that cleat before fully tightening the bolts in the direction you want it to go. Then the “float” setting will apply some light or moderate spring tension and allow your heel to rotate inward if need be. Clipless pedals with good cycling shoes will greatly enhance your riding (in my estimation).
Also, if you want to start back to riding on trails, that’s great. As you become more confident, roads are where it’s at. You get much more climbing and descending which correlated to more excitement.
Don’t let a traumatic road experience from 30 years ago jade you. I’ve heard of many riders who crash or have a mishap - they barely miss even one day after that. Everyone crashes at some point, you can’t be protected from everything.
Bike trails are great ways to get out of town but it is the crossroads out in the lesser populated areas where things get interesting.
As for bikes - get what you like! And be prepared to make minor fit adjustments as you continue to drop weight,