Get yourself out there and start making your name known to others - develop a personal brand.Identify someone you want to be like - someone you admire and respect - and see if they’re a person who can impart their experience and wisdom to you.

My existing portfolio definitely hews toward working poor, but in areas where the locals tend to keep their yards up and have at least a bit of self-respect.

You mention not having much credit established, but do you know what your score is? 

The law also established a slush fund for "legal services for tenants", meaning that we can be sued with our own tax dollars.

I don't mind committing 2-5 years to get everything running and established, so long as by the end of that time frame any portfolio I have is set up in a way to set it and forget it.

Tenant screening is more than just reviewing applications and conducting background checks; it’s about ensuring that your property is leased to responsible tenants who will treat it with care and respect.

Please learn respect sir for future reference.   

The wholesaler probably doesn’t believe the deal will close, just wants a contract from you and sellers failure to sell as agreed so he could establish the lost profit due to seller’s non performance and sue for the $15k differential which is easier to win rather than specific performance. 

In many cases, the old tenant base doesn't fit with the new plan for the property (ie upkeep, cleanliness, and respecting the rights of others).

5 years ago, we were both working at Dunkin Donuts and Domino's respectively.