One of the cleanest / most modern / most energy efficient (for its size) houses I've ever seen was built in 1837.

fbclid=IwAR3KzMc3T_hmVfCrbY-uWUqQ1xnJtbFIVFJ8ikN-tRSO268N7WU_nH-bAugThere are lots of stats and tables, but to save you the energy, this is the specific one I was referring to: Utah is close behind, has us beat on the 30 year mark.  

Should I being looking for a GC to give me accuracy and reliability or is the license more of just a bonus when searching for reliable contractors?

It might just be easier to sell and roll the proceeds into a cash-flowing MFR, either here in CT or down in FL, assuming you have a reliable team there.

Only contact I have for SD is a reliable handyman. 

You can force any strategy, but the amount of time/energy to find that deal is going to be much higher than taking what the market is offering right now. 

What are some things we can consider improving that will have lasting value but won't be a total waste of time/energy/money?

Has anyone on BP had luck in the Ann Arbor or Ypsilanti area finding other good, reliable, reputable PMs?

Just cut out some extra energy drinks, too.

I am beginning to lose the knee-jerk aversion I've held towards Gary but whether or not we invest there depends 110% on finding a reliable PM.