We could sell that house by itself, but it would be sold under a land in common agreement and an HOA would need to be formed.I also confirmed with the Public Works department that a 2nd driveway can go in, with a septic designer that there's room for second septic tank, and with the public water company that they can tap into the main water line from one of the neighboring roads.I'm sure there are some more details that I would need to iron out that the code officer didn't bring up, but the high level answer I was looking for is that my town does allow selling off a second house under the LD 2003 legislation.

We found the deal off the MLS there was an investor/realtor who owned it (inherited) and didnt want to bother with reno so we took it off his hands for $175,000 put in $90k/$100k & ARV $350k-$365k max.

When first learning about real estate, one quickly realizes there are about 10,000 different ways/markets/options for investing in real estate. 

The Person is wanting to sell me their home for the amount of Equity they have built in it right now. approx. 20KThe Seller has agreed to Let me Lease to own and sublet the home and continue to run it as I see fit. ( i am going to keep it as a AirBnb)Is there a way transfer me onto the deed and then refinance the house out of the VA Loan and into my name?

There are a lot of tricky rules around this, and I believe Freddie either just changed or will be changing very soon to require 1 year of property management/landlord experience in order to count future rental income when buying a new property.2nd question: All debts in which you're obligated, regardless of whether they report on your credit report, are considered in DTI.

If the property is nearby, I would have gone there myself to A. get the measurements and determine what color to replace with.

There are tons of great local Chicago meetups that are worth checking out. 

The tricky part to this transaction is the house was just purchased this year with a VA loan, so there is no equity.

The 2 main issues are that there's a leak in one of the bathrooms that is causing water to flow under the sub-floor and into the crawlspace. 

At first glance though, it doesn't seem there's been much appreciation there in the last 5 years.