And while ultimately I'd like to have a multi unit of my own that I actually house hack, for now I get to live in a first class building (maintenance free) on a non-first class budget.

I don't have a specific answer because I don't have experience doing this yet.

What I'm trying to understanding better is creative financing, analyzing the surrounding markets, making connections, and many of the other industry-specific concepts that can really only be learned through real-life experience.The idea of REI came about between myself and my friends because one of them has access to a large amount of capital that he received from his parents as a gift.

I would also market the property on local Facebook groups, you may find that there is a specific group for STR owners in the area. 

I'm working on purchasing my first commercial building here in CO Springs (80909 specifically).

This includes having team members that specialize in each specific part of the process, spotting macro trends quicker, and buying consumables, furniture, and other services in bulk.

She is new to the mid term game and i don't have any managers that specifically have people that work with insurance companies or possibly nurses and whatnot. 

My utility company does budget billing so it is the same price every month.

Maybe you could be more in a managerial or teacher role to others that need guidance in that specific work you have done in the past.

I was referred to a great GC that is helping me stay near budget throughout this endeavor.