I’ve hit a challenge in shifting my mindset and would like to ask the group - if I’m not an extrovert with a sales background and the cushion of a 6-figure corporate job, will I be able to succeed at REI?  

It's a challenging market but I say if you can pay less then you currently are renting then it's a win.

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.

In that case, you’d typically need to file a legal challenge, which could involve going to court and showing that the restriction is unnecessary or unreasonable.The best advice I can give would be to consult a real estate attorney to understand your specific situation and options.

The challenge we're facing is the lack of short term rental data for the appraiser, and we won't know if it will meet the debt service coverage ratio (DSCR) requirements until the appraisal is complete.Has anyone dealt with a similar situation?

When analyzing properties, it's helpful to run a rental stress test to see if the deal can withstand unexpected challenges.

Challenges?

I wasted too much time trying to piece it all together and when you're in different states it's all the more challenging to make sure everything is legit.

When you've housed thousands of people things do go wrong, but looking at those challenging occurrences, learning from them, and improving, is something we're committed to.Thanks again, and if you have any questions or issues please feel free to reach out directly.

I think BRRRR would be quite challenging as a first deal in an out of state market, but that is just my opinion.