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...

I would advise you to consult with your tax professional to see if you may be able to use some planning strategies to help you best take advantage of the deduction in 2024/25 in the event it isn't renewed by the next congress.

I will join the FB group and I also plan to attend the MTR summit in San Diego next month.  

In a chapter 13, the debtor is required to submit a chapter 13 plan that proposes a repayment plan over a term of 3 to 5 years and allows the debtor to restructure debts or other obligations. 

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

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.

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

What were you looking for in other markets that you couldn't find and you believe makes Milwaukee a better fit?

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.