This is more of a reach goal for me since I am still in my "collect 4 green houses before trading up to a red hotel" stage, but I thought I would ask the hive mind anyways.

Keep in mind you will probably have a deductable to pay first.

Also keep in mind as time goes on typically your yield will increase because of the rent growth. 

I would want them to know what's going on and to LISTEN to what their frame of mind is.

What type of RE role were you doing at that time, if you don't mind me asking? 

I’m still new to real estate, so my knowledge might not be perfect—please be mindful!

---The way my mind is thinking, this should be eliminated by paying off the mortgage with the WLI cash value policy loan.

Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

Also, keep in mind that if you do form an LLC, you'll want to keep these under your EIN, not your SSN.Bank AccountCredit CardTitleLoanBookkeeping Ledger

You can look into low-income neighborhoods usually the properties are of lower value, but I'm not quite sure if that applies everywhere but I know in Florida I see it here and there, and if you need help looking I don't mind helping.i would be wary about REO/HUD owned properties as a first time househack.