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. 

The low hanging fruit has already been picked.  

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

Tenants, "go into Holiday-mode" and start spending disposable income (and racking up their credit cards) on Thanksgiving feasts & trips, Xmas presents & trips, and finally NYE plans.3) Income Tax Refund checks start being received towards the end of February and corresponding, the rental market starts picking up again as tenants payoff their “Holiday Hangovers".4) Spring Fever starts, sometime in April-May, causing both sales & rental markets to start picking up.

In fact, many of their stories, just relied on, picking up a few investments in solid areas, taking care of them, and holding onto them for a long time. 

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

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?

You can do some sourcing yourself through Facebook groups, and online RE communities , and even pick up the phone and cold call some homeowners that may be tired landlords, don't owe anything, and have built up some equity.With enough volume, you should come across some solid deals.  

@Anne Christenseninstead of picking a market based on statistics or numbers, I'd pick one based on... 

They pick it up.