I am currently self managing 8 units in the Chicago SW side predominantly in the Lawndale and Oak Park area a mix of FM and section 8 tenants.

Section 8 tenants are also nice as the government will help pay the rent.

The repair was extensive and costly, requiring excavation (about 3x6 feet) to replace the broken section and clean up the mess.

My plan is to add 2 - 6 shipping container type of small houses and an above ground pool at some point to make at least a section of the property short/mid term rentals.

Seriously though, if you haven't already get your self a solid real estate-focused tax professional in your corner.

I actually look at this section when I'm doing a market analysis.

They require 48-72 hours notice to schedule anything onsite so we've been waiting 2 weeks now for a Section 8 initial inspection date to be scheduled by them.

My piece of advice would be to make sure you have a great agent in your corner to help you assess the market, make informed decisions, etc. having a good agent can be day & nights difference when it comes to your experience.

., Purchase Price: $475,000 ($197.9/sq. ft.).Estimated Market Value: $402,000 ($168/sq. ft.).Financing Terms: 2% interest rate, with a 9-year balloon.Unit B Income: $2,049/month (Section 8 tenant through November 2025).Unit A Income Potential: Similar rent or higher; Section 8 cap for the area is $3,234/month.Monthly Loan Payment (P+I): $1,386.Cash Flow Breakdown (if both units are rented at $2,049/month):Gross Rent: $4,098/month.Vacancy (10%): $410/month.Operating Expenses (37.3%): $1,376/month.Net Cash Flow: $943/month.Key QuestionsWould you be comfortable paying an 18% premium for financing at 2%, especially in a market where current mortgage rates are closer to 7%?

Yes, the government pays the Section 8 rent timely, but more and more tenants are having to pay a portion of their rent.