Once you have a property in mind, getting a few estimates will be the best move.

If you had to start over today with limited resources, what strategy would you focus on- Would you start with house hacking, BRRRR, wholesaling, or another strategy?

What would you do in this situation or is there another option I am not seeing?

The main house(first and second floor) is in reasonably good shape for a home of this era - most of the original woodwork, flooring and tiling looks good.

The house is a smaller colonial with 3 beds and 1.5 baths.

All, I understand that to be a property manager in Colorado you must be a licensed realtor. 

The $1,100 has been nice for house hacking purposes but when looking at this as a remote investment your question helped to put some numbers down.The main property leased at $1,850 in 2018/2019.

Most are in HOAs that are designed to be investor unfriendly or downright prohibit rentals. 

These are rental houses and NO one is 100% perfect with rentals houses I dont care who you buy them from who your tenants are or who your PM is..

But you also SHOULD have some vacancy and some capex on an 80 year old house.