Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.

Totally understand that those things don't closely mirror the BRRRR model too closely, but that's what I'm seeing right now. 

Make sure you understand the auction process and are prepared for any unseen issues with the property.Auction Considerations: With auctions, pay close attention to the condition of the property, title issues, and financing restrictions.

Quote from @John Davey: Id appreciate any help, as ex. if i take out say 100k home equity loan and use 50k each as down payments/cloing costs my understanding is i cant deduct the interest?

Pick up the phone or stop by local code enforcement offices to make sure that you have a crystal clear understanding of local laws and regulations.

The more you understand the local market, the more value you can bring to a mentor.Stay persistent and consistent.

That pragmatism will help you mitigate risks as you understand the different components of managing rentals   

Understanding the Product mix.

As I am new to this and looking for cashflow using rentals, one key aspect of this investment is to ensure that the unit rents out quickly and while I do understand that cash flow to begin with might not be attractive, it can be a good investment in the long run if the location is right(as appreciation also kicks in).

If there is a due on sale clause in the loan doc then it doesn’t matter what the loan officer told you verbally.I’m not an attorney, but from my understanding of the loan is still in your name personally a good litigator can pierce the veil and your LLC protection wouldn’t amount to much.