This is a challenging market to find cash flow in, but it can be done. 

These are difficult to make good cash flow with any business model.

They can hook you up with these contacts, making your real estate journey smoother.Since you're looking to cash flow, I'd suggest you take a closer look at Cleveland's Section 8 market, its known for reliable government-backed payments and high tenant demand.

Are you cash flowing the property?

Do you have any other properties that cash-flow? 

But after speaking with a local investor-agent, he felt pretty strongly that a first time investor should just scratch BRRRR from their vocab and buy something nearly turnkey, collect the steady drip of cash flow for a few years, and save up for property two via W2, and then start to think about BRRRR.

However, due to short seasons, and more mild winters, I'm struggling to think even 3-4 years from now that I'd pull anything more than $50K a year in rentals.Bills / property taxes are about $12,000 a year.The thing is, being single, and not really dying to work in this area (small town), I'm feeling rather stuck, as is all the equity.I'm currently not working, but very much want to move back to Chicago, a place I love, and start buying cash flowing properties.I'd suspect I would have about $900,000+ after all is done if it sold at $950K, considering the vast array of other things I've accumulated (wood splitters, machinery, tools, MCM furniture, rugs,).

what you will find if you do this is that almost nothing on the MLS in a good neighborhood is going to cash flow right now.2. how to determine rents - COMPS. 

We used STR cash flow to rehab the entire home.

Then I take that $75k left over and buy a $300k property with it the provides me cash flow and in five years may be worth $330k and the car would still be worth $15k.Thats why.