If the separation of funds was for asset protection (in this case there was another reason), it is my belief that an umbrella policy is easier than trying to maintain separation of assets especially when the property has been purchased with individual’s money and financing.  

By prioritizing fundamentals over chasing ROI benchmarks, he’s now sitting on an asset that’s appreciated 30% and maintained strong cash flow.Personally, I once miscalculated reserves on a triplex I bought early in my career.

I’m Hey Adam, totally can relate with you being from an expensive real estate market - I moved to Columbus a few years ago (from Portland, Oregon which was super expensive) to become a full time real estate investor, and ever since, I've completed quite a lot of BRRRRs, flips, and own a successful rental portfolio here in Columbus Ohio.

Personally that would be a pain to maintain and do lol

Bananas and pineapples become something kids learn about in books and from us "old timers' recounting stories of the taste.You want a fast track to apocalyptic USA, austerity measures is the ticket. 

The fact that you think the tenant is a pain has nothing to do with how you maintain the property, you could be creating legal and maintenance problems for yourself by not taking action. 

I was even able to travel to a country I always dreamed of traveling to since I was a child whilst maintaining my airbnb from across the world (Japan). 

Our other 3 buildings (two duplexes, one 3 unit) are basically stabilized at this point so just continue to maintain them and build the reserves even larger from the cash flow they spit off.

However, if you are an out-of-state slumlord, you can now pass 100% of the financial and legal liability of maintaining a property onto some poor local.

Focus on building and maintaining active income first.