Not having experience qualifying prospects I would think that the leads you would get from here, if any, would be..... challenging. 

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.

Challenges?

My approach is to take a few minutes per quarter and make sure it is accurate by manually checking my true competition and adjustmenting prices accordingly. 

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

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.

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?

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

As a smaller, self-managed landlord I think solutions that offer that kind of scheduling/logistics framework are solving for one of the most long-standing self-managed challenges we've had for years: how to scale and systematize operations when you're are landlord or PM out there hustling for your next deal.