House hacking will also give you some personal "property management" experience.

Current interest rates are going to make it difficult to reinvest into real estate and not come out of pocket more than $1000 annually, per your current situation.I am also assuming you are paying a property manager with your current figures. 

I like STR but the maintenance gets expensive and frustrating to manage or do myself.

Most management companies will tell you that games rooms definitely increase revenue. 

Include not only the mortgage payment but also taxes, insurance, property management fees (if applicable), maintenance costs, vacancy allowance, and any planned capital improvements.

We own & manage a few Multi-Family properties in NorthWest Brooklyn (Park Slope, PLG-Lefferts, Bushwick) which I've been managing without issue for the last several years myself.

This is why you always use a property manager.2.

A virtual assistant could easily help with the day to day listing management, guest communication, and other virtual tasks.

With the second one, I told them I was the property manager.

The out-of-state seller utilized a typical property management company which resulted in bloated expenses and a rent roll below market levels.