My plan is to raise capital for the down payment through an investor and create an LLC with my father to get approved for a DSCR loan.

Just saw this on the local news this morning.Nothing changed yet, but maybe soon.https://louisvilleky.gov/government/planning-design/middle-h...

The plan is that the space between the sleeping area and another living area will have a closet with bi-fold doors.  

Hey @Ryan Marble, it is something that you can do no problem, like the others have said.Regarding figuring out your return, take some time and look at all the listings that would be similar to what you are planning on AirBNB and VRBO.Look at their nightly rates, occupancy and amenities.

I shifted focus but def plan on going back to the strategy and ultimately plan on graduating to deeds so I can acquire the land. 

I run a small private real estate investment club and we love to plan happy hours for visitors to Milwaukee.

How feasible is this plan from the POV of a seasoned investor?

Planning to self-manage remotely / family in town close by in case of immediate action.

You could add a clause in the lease stating the penalty for late payment.I like the idea of electronic locks.I would identify the items that need updating and plan accordingly; roof, furnace, etc.

This will allow you to acquire more rental units and also being able to use the vacated unit rents at 75% to help your debt to income ratio DTI.There is a FHA 100 mile rule if you do plan on using FHA on your 2nd house hack.