I knew that it was undervalued when I bought it.Generally speaking, brokers make cash flow seem rosier than is the actual case by leaving various expenses out. 

He helps out with the trash and keeps an eye out, so I was cool with leaving him alone while I concentrated on the other units.It was okay till I finished renovating a couple of the other units and created storage and laundry in the basement, where their studio apt is.

The house is 1200 sqft and we'll be leaving the attic alone and focusing on the basement and 1st floor, which is where the 3beds/2baths are currently.  

Do some people just leave grout between the drywall and the tile?

@Gabriel BenavidezIf you are self-employed (i.e. active self-employment earned income separate from your w-2 income) with no full-time w-2 employees, you can set up a Solo 401k and then rollover your 401k funds once you leave your current job. 

If you really feel like rewarding them or trying to keep them, leave the rent 10% below market but not more than that. 

He will be shortly leaving a high pay stable job (military pilot) for a low paying (40k/yr) job and it looks like this transition might be preventing him from qualifying for a cash out refi.

we buy listed non financeable properties all the time.. so does networth or what ever other big wholesale RE brokerage in your area they are right off of MLS.. whats the difference of you bringing a wholesale buyer through the house as opposed to a retail one off of MLS.. answer NO difference.. my thought Is sellers in these instances think they are saving commission but the sales price is lowered to reflect it and many times wholesalers just rip the pants off of sellers leaving them with 10s of thousands less than they could have gotten with a property open to the market not just a wholesaler who has his own best interest at heart not the sellers. 

Meaning you'll probably leave ~$8k in the deal, which is fine.

Some wholesalers will help guide you as well, but you have to be careful because they are trying to sell their deals and will shine the light to make them look as good as possible.