With a 7% interest rate and high HOA fees, the key is evaluating if your skills and investments can generate higher returns elsewhere.

However, there's a critical detail that many tax advisors conveniently overlook when promoting these studies.Here's the uncomfortable truth: If you're a high-income earner (AGI > $150,000) and not actively managing your properties, those promised tax savings might be locked away for years.

Let’s break this down:The case for holdingThe 4.75% interest rate is a valuable asset in today’s high-rate environment.

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

When investing in high cash-flow markets, I always recommend working with an investor friendly agent so you're able to gain the right insight on the different areas and the risks involved.

Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

But I see people turning long term or highly appreciated primaries in to rentals.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

DSCR loans go up to 80% of the purchase price and depending on the Debt Service Coverage Ratio and your credit score you can expect rates on a 30 yr loan ranging from High 6%- Mid 8%. 

I think the key to getting a good start in REI is finding a way to have a high 9 to 5 income and using a good portion of it  invest in your real estate endeavors.