Cutting the trees, fix broken doors, touch up. 

Water Stains in Sub-Floor under toilet (Structure safety and mold/fungal growth concerns) Discolorization of floor joist due to harmful form of fungal growth Door hinge on bottom crawlspace Floor Deflection, sag in master bathroom and bedroom b) The girder in the middle right end of the crawlspace and the floor joists at the rear of the crawlspace have been notched in several locations to install plumbing lines and the headers that were installed where a joist would have been cut in two to install the drain line under the shower stall in the master bathroom are not properly attached and exhibited signs of failure.

He may be desperate or he may simply be a hobby landlord.

Capital gain - no problem as long as your intent was not primarily to simply resell as a flip like @Michael Plaks said. 

A refi like that does not simply put the refi proceeds at risk. 

That is not  meant as a criticism, simply that is not what they specialize in. 

I've been holding onto my W-2 income simply for the allowance of getting a home loan and realize once I convert full time 1099 my chances of getting the loan decrease significantly.

I want a property management team to start off with, simply because I don't know the ins and outs, and need people who make this their business.

You will simply have to just add these costs into your analysis to see if it is worth it.

As a small time RE investor (two properties), I'm thinking it just makes the most sense to 'shift' some of the deductions I used to enter on a Sched A over to the Sched E because of the new rules/deductions with the Tax Cut & Jobs Act.