Dude I love it. You are definitely a few steps ahead of me but I love the motivation! Contractors right now as you are aware are tough to deal with. All of them, even for me. I have my electrician, my plumber and my HVAC (who work for themselves or a W2 employer) and my own carpenters (who work for me).
I can feel your pain on towns, I sort of wonder if there are better towns and worse towns to deal with and being a landlord/propery owner. I know the town I reside in is difficult at best to deal with.
I think everyone wants more time and money. I would suggest reaching out to a good friend of mine (who as far as I know is not on the forums). His name is Dave Haberfeld and he is a real estate and business guy. He is primarily out of Bristol but has branched out a bit. The reason I mention him is I feel like he is operating at your level or perhaps slightly above (that is not an insult I hope I just know him better than I know you). I feel like he may be a good fit as far as mastermind or if not I know he will know who to send you to.
If you do Facebook - feel free to add me over there or PM me you phone number and I can connect you guys.
All the best and hoping I can look "up" in a few years and see myself in a favorable situation such as yours!