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. 

I am attempting to find funding. 

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

Good questions to start with @Kyle Jey - this gets my wheels spinning.I will self-manage and I live very close.Landscaping, snow - these are not factored in besides the maintenance percentage (5%) I listed in my post.I have no idea if the place needs rehab; all units are currently occupied and there are no images of the inside.Closing costs - hadn't thought about this; would attempt to roll into the mortgage payments - maybe $100/month extra?

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.

With $300k of student debt hanging over your head simply qualifying to buy additional investment properties will be extremely difficult cause your debt ratios will be totally blown out. 

PS one of my very short stints was attempting to sell dental equipment door to door.. you know high speed drills low speed and delivery systems and chairs and lights etc.. sit down dentistry was just starting to take off.. turned out Dentist before that had a huge problem with back aches.I worked with a start up called healthkit.. they had a delivery system way ahead of its time.. it was all numatic and was used in the military because the holder of the drills was solid aluminum block 2 X 2 X 6  with no moving parts.. unlike in those days the ones that looked like something out of a sci fi movie and would break all the time.. but of course ours was the most expensive and well .. being that and being the industry was very difficult to sell.