Playing poker there are signals sent to other players called "TELLS".Until you have control of a deal, don't talk, keep your cards close to yourself  and mute your comments.It's nice to be friendly, but this doesn't help when you are trying to control a deal.You need to find the owner of this estate, who is it assessed to, where are they, has it been listed in the past, is it in tax sale.

You're basing your entire deal on future events (way in the future) that you have absolutely no control over...or guarantees that the situation you need at that time will ever take place.

My understanding that recurring maintenance is acceptable like pest control, lawn care, hvac servicing but what exactly is a normal repair? 

When you use third party collectors who do not give you PCI compliance, you are subject to charge backs for which you have not control over. 

To clarify, here's a breakdown of what we have:Income Tax and Bookkeeping business- Sole P in my wifes name (getting ready to convert it to an S-corp)Hair and Nail Salon- Single member S-corp in my nameWife is self employed as an S-corp (she booth rents from the salon I own)Commercial real estate LLC - 5 unit commercial building (wife and I are partners)Commercial real estate LLC - single unit commercial building (wife and I are partners)Residential LLC - Holds all SFH's (wife and I are partners)Master LLC that controls every investment property.I know we have a lot of moving parts.

Right off the bat we first fixed up a bunch of stuff.... added a gate with key-pad access control.

I do not rehab properties myself though, so if you are handy, expenses may be able to be controlled, which would change the numbers for the better. 

It's not a lot of extra money up front, and it's well worth it in 3 years when a control board breaks.

Mitigate as many risk factors that I directly control as possible.

You may have to consider a creative strategy to get them out like a pay to leave situation if they resist: offer to pay for the moving truck or application fee for the next place or even give them the last month for free...anything to get them out and get your unit up to market value so you can maximize your cash flow.A few points to note before you take action - be sure your area doesn't have any rent controls or laws restricting landlords from raising rent.