It is always valuable to be able to walk into a property an analyze cost to repair, it is a huge factor in determining the feasability.

I could see this fit into several categories of 'real property trades or businesses.'

If you want me to go into further detail, I'd be glad to do so either on here, via PM, or even just call me.

I will look into using what you said. 

Anything you pay outside of that can be challenged.I would make that payment into a dedicated bank account until you get the necessary paperwork.

Other analysis you can do is analyzing your cash flow, passive appreciation and principal recapture to see the total picture on your ROI.Once you do the analysis, you may find putting money into maintenance may or may not be worth holding the property.

But I don't know that I would jump into real estate just yet either.

I have managed to get myself into a bit of a complex situation on my first deal and I'm looking for some advice. 

It would split the single parcel into two parcels, one side would be legal conforming 4-unit & the other legal conforming SFR.Thanks in advance!

That is taking into consideration employees and 65 rentals, so I am sure you will be a lot cheaper.