I'll be getting several more opinions from other plumbers as well.  

I'm sure how far Lake Monroe if from the University but I would also look into the amount of STRs in that as well.  

My plan is to funnel the rental incomes from all three properties, along with my W2 income, back into the HELOC while covering all expenses from it as well.

I've been reading a ton here as well and am learning every day.

I was thinking of starting a rent increase for my 1 bedroom tenant voucher due it being low and well under fair market value(Based on  hud and zip code) but my tenant is in the process of having a caretaker for her disability and getting approved for a two bedroom voucher.

That "pipe" is known as a Line Set. 

Well worth it IMHO given poor performance of RTO/seller financed zillow listings. 

Investment Info:Office Space commercial investment investment. 100's of completed projects, JC Beal Construction is nearly 100 years in business, Beal Properties manages well over 2000 doors all throughout Michigan and the Toledo, OH area.

I live and invest in Milwaukee since 2007, so probably a little bias here, but we are set up very well for future growth. 

It very well could become a large enough investment to be worthwhile, also solving for "unexpected emergencies ", for the most part and would an easy self management situation if you were to live onsite in one of your connected townhomes.