My only reply here is to say to simply focus on the business objectives.

I know some people have the knack and others simply can't make it happen.

Simply gifting him half the property now wouldn’t immediately allow him to claim the exclusion without fulfilling this residency requirement, I don't believe.One thought would be to use a HELOC to pull just enough equity out of the current home and use it to buy a smaller home, or at least the down payment.

Considering that, you are likely going to see appreciation year over year, which essentially will be additional equity you'd capture just by simply living in the home. 

I know that’s not the only reason to invest in real estate but simply put it’s what I’m mainly looking at and In the markets I am currently looking at, it look like regardless of str, mtr, and ltr, I’ll be cash flowing around 150-300 a month.

If the eviction goes to court, then there is a record of that eviction on their file and it will make it harder for them to find another place to live (assuming the landlord does a background check).Not renewing the lease happens when either party decides they simply don't want to renew the lease. 

It turns out that we were never going to get paid out in the first place, and eventually found out some of my properties closed, but was still never paid out for them, but most of my properties simply just ended up dropping and i was never informed of it.

Walkthroughs are never detailed enough to be final (ie often tenants have lower disconnected and discover broken appliances later.) 

For your existing vacancies - there are no proactive measures - simply active or passive measures you can take.

Worst case scenario, if that doesn't work, I can simply do fertilizer applications and landscape lighting as they don't require much labor.