As the situation became more complicated, I involved a lawyer and began mediation.

He spells out how to invest in other markets from a distance.I do think you are over-complicating it.

It’s a nice idea to offer streaming services for renters, but it can get complicated.

It's really beyond complicated to even try this and silly to pitch to someone who is a colleague.The best person I have seen be able to move STR deals for other investors, and some on sub-to, is @Zeona McIntyre.

A fair warning, you'll be wading through complicated info.  

I flip in areas I'm familiar with but even if not, it's not complicated to formulate comps from basic google searches.

the "too complicated" part is the partnering. 

Keeping them in the loop could help avoid conflicts or complications down the line.Lastly, think about framing your case around fairness and practical impact.

For example a price below where I think it will sell for, attracting more Buyers, but not too low where I'm doing unnecessary work filtering out Buyers who don't understand the market conditions.

Quote from @Rud Sev: A quick follow up that I have (I understand things can really quickly become complicated): if there is cash flow, and that cash flow is larger than any depreciation (assume no cost segregation), K-1 reports a gain, is this gain considered to be ordinary income please?