Just hit me up, or me and two other agents run a monthly investor mastermind tailored towards newer investors here in Denver. 

Zero  were tri's and quads mainly due to the self sufficiency rule for a primary residence.Regarding you question for analyzing, I have a comprehensive spreadsheet we build tailored towards House Hacking along with a youtube video tutorial how to use it.

I'd day the last 20 or so episodes have been tailored very specifically towards the STR market.

Are their any companies out there (hard money or conventional) that have programs that tailor to this situation?

Shyla Tailor https://www.civicfs.com/

It would tailor to your personality and what you are looking for and the money spent is well worth the issues if you get one that someone else drafted or used as a templet.

Also, it’s worthy noting the appreciation rate margin of error is 2%, so you can tailor yearly projections up to 2% below or above based on your risk profile.

I like it segregated from my personal stuff and the coverage was better tailored to rental property than what Allstate offered. 

So if I can look at a market that is primarily booking on VRBO I might decide to tailor my listing to an older or family oriented audience … or the exact opposite for an Airbnb market.

However your circumstances are your own and thus will have to be tailored to you.