Hopefully by then, I would have kicked the tar out of analysis paralysis and have some deals underneath my belt.

Generally speaking encouraging people to try to time the market and steering them towards high risk strategies is bad investing advice in my opinion, and yes I would place OOS investing for high cash flow in the “high risk” category, possibly the equivalent of buying a stock with a 13% dividend yield thinking that’s a smart move because the cash flow is great when in reality the company is likely desperate to raise cash and approaching bankruptcy, just like rust belt properties with high cash flow might seem good to a short-sighted investor, when in reality those properties are cheap because locals have witnessed decades of out migration/ industrial decline and realize those properties are on the cusp of economic and functional obsolescence.

I'm also new to REI with only one property under my belt.

Plus they have a very nicely designed tax-advantaged 1031 exchange conveyor belt, which allows you to defer paying taxes indefinitely.

In a recent podcast that interviewed Brandon Turner that I heard, if you listen in between the lines, you’ll discover even he is having enormous challenges with his apartment building in Cincinnati.It’s likely why he’s more excited about his mobile home parks and syndication deals now.It’s a common theme through the Midwest,I think.Don’t just talk to brokers and local stake holders with vested interests...Speak to investors who have actually risked capital.They’ll tell you the cold hard truth about investing in the snow belt.

Once we have a few deals under our belt, we will be using that money for a down payment on a fix and flip and then a  rental property 

Once I get enough transactions under my belt I will get a broker's license so I can manage other investors properties. 

With property values falling and companies tightening their belts or even laying off employees, there's no better time to make sure your mortgage meets your current budget and long-term needs.What Is Refinancing?

I am constantly educating at this point to try to add to my tool belt!

Additionally, billing the tenants is extra work that you will have to do each month, which could start to seem cumbersome if/when you get more doors under your belt.