Some areas that are on the path of appreciation and aren't yet completely picked over include Little Village, Hermosa, Belmont Cragin, Mckinley Park, etc.I am a local investor as well as an agent so if you need any help please don't hesitate to reach out

You can pick up some scraps, but it will be tough and intermittent.

Have you picked a market and strategey yet?

After the election and purported rate cut(s) from the FED, I expect buying activity to pick up rather noticeably, which means more competition and likely higher prices. 

Are they picking window style and placement, exterior cladding, color, etc? 

Picking a house with major, costly structural issues or in a location with poor rental demand can hurt both the rental and refinance phases.

The low hanging fruit has already been picked.  

I wanted to share the financials after 3 years, and demonstrate what three years of real estate investing can achiev3 Bed/1 Ba Single Family Pro-Forma:Year 1 (2021)Income:Rent: $1,200.00Expenses:Mortgage: $509.95Taxes: $119.10Insurance: $43.84Cap Ex: $60Repairs/Maintenance: $60Vacancy: $60Monthly Cashflow:$347.11/mo or $4,165.32/yrYear 3 (2024)Income:Rent: $1,300.00Additional Pet Rent: $75Expenses:Mortgage: $509.95Taxes: $155.43Insurance: $53.03Cap Ex: $68.75Repairs/Maintenance: $68.75Vacancy: $58.75Monthly Cashflow:$450/mo or $5,400/yr (Total/Not 50/50 %)Total Equity: $37,473.88-Principal Equity: $7,959.62I have learned a lot about the systems needed in place to run a rental property, and how important picking the right tenant is. 

Very unusual and foolish for a lender to allow a borrow to pick the appraisor. 

For the sake of trying to learn and picking your brain, why would it be better to keep one rental and upscale the other instead of selling both and getting a significantly more expensive piece of property and trying to significantly increase cash flow?