The quality of your tenants are what will have the biggest impact on your happiness.

I think the biggest piece of the puzzle is to identify which category you fall in. 

My biggest asset is my mobility, since I'm single and travel 80% of the time for work on a regular basis.

In my experience those programs are more comparable with the coaches on "the biggest loser" than being a purchased magic pill that suddenly makes all the changes, so either way it's gotta be you who does it, only question is if on your own or with an expensive coach chasing behind cracking a whip on ya to keep you moving forward at it. 

Another down side is that He is paying $700 and current rents goes from $800 to $850 a month.

The biggest challenge was closing as COVID-19 was hitting the population and beginning renovations on the property while preparing to reside in it and both of us deploying in the next year.

Some of the downsides have been articulated above.I second the suggestion to network with NPN investors who buy in the areas that you want to rent in. 

I really can't think of a downside to having your real estate license. 

@James Kim I think that @Dan Heuschele and I agree that cash flow is not the biggest contributor to ROI and you have a high ROI but not a high cash flow on this property so far and likely in the future.

In theory yes and in the short term yes, the biggest gainers from remote working trends will be outlying areas like Santa Cruz, Napa etc versus out of state location s like Montana or Idaho etc.But I also think once Covid talk dissipates office culture will take over and old habits WILL return.