I recently came in contact with a RE investor who is farther down the line in his career than I am.

This way the wider outside lip contacts the entirety of the drywall while the wings are being deployed and tightened in place.Is there a way to pull the already wired, "old work" electrical boxes through the drywall cutouts from the inside out while not making the holes so big that the wider, outside lips of the electrical boxes can't properly provide contact to the drywall so it can be tightened via the screwed wings?

Contact a local closing attorney as they may have one for you to use. 

This is what I recommend to new investors who contact me asking if these numbers look good. 

I really like the idea of leveraging local contacts for walkthroughs and feedback.

I'm contacted by another landlord in the same town who needs help with a problematic tenant.

Try connecting with local landlord groups (BiggerPockets forums, local meetups, or REI groups) for referrals.Property Management Companies – Even if you’re self-managing, you can contact local PMs to see if they have a handyman they recommend for small jobs.

I'm seriously considering trying to find something there, but need to build up my knowledge and contacts of reputable agents and contractors etc.I'm interested in multi-family, STRs, commercial, self storage, and possibly even flips if the right opportunity came up.

A couple of years ago, I worked with an investor who never updated the contact information for the loan and the Bank call the seller (ex-wife), that day she was mad at her ex-husband and told the bank her ex allowed someone to steal their property from them and they got no money, she was kicked out of her house and there were strange people living there.This could all have been avoided if the investor did this process correct.Get educated, also I do not know your attorney but not many attorneys have the knowledge to do this process correctly. 

Now, I need from you a contact at a title company and a contact for insurance.