Happy to help you bring the goals into focus and advise on all aspects!

Should I hire a local PM company for the short term to make the transition and then after 6-9 months move the PM software?

I lived there myself for 4 years, then moved out and converted it to a super-profitable short-term rental (it's ideally situated near great restaurants/nightlife, the National Zoo, Rock Creek Park, and hotels that host professional conferences).

I am managing the MTR and hired a property manager for the 3 long terms) and am trying to set goals for my 3rd property- hopefully in about a year’s time.

After experiencing different types of inspections with all kinds of properties from custom builds to existing, it all depends on your end goal , I highly suggest you reach out to a team, really strong team such as @Jorge Vazquez.

I have been self-taught about investing, retirement, taxes, and various other financial things but have never learned much about real estate investing beyond owning a home and maybe renting it when you move.

Goal is FI by around age 50. 2 boys (5yo and 7yo). 

I was also thinking that this may lower our office building payment which is good for our personal cash flow with other investments moving forward.Thank you all for the advantages/disadvantages and I hope this doesn't come off as an irresponsible thought.Kegan

The goal is to build & sell, but worst case scenario maintain the property for a couple of years if it doesn't sell.

Once you're ready, create a goal (e.g.