This is where you need to rely on other investors - or a very competent contractor. 

Had an issue with being able to transfer the mortgage to my LLC (which thankfully the lawyer caught as it would have really been a bad situation), so I am relying on liability coverage to protect myself and my personal assets.

Commercial banks rely heavily on the stabilized value that an appraiser provides. 

These markets typically have lots of competition, higher home values relative to earning potential (since most homes are essentially valued like hospitality assets instead of homes), and lower regulatory risk since the local areas have embraced STRs (rely on them for taxes, etc.).

Should I rely on these one-stop-shops?

I also have to potential to roommate with a family member which I would charge them $800 a month for, don't want to rely on this but it would help.

She doesnt rely on this house income. 

I've been with eXp for 4 years and am licensed & active in 4 States-  after working with a 'bricks. and mortar' brokerage in the Washington DC Metro area for 15 years, I can tell you is that what I love best about eXp Realty is that it's allowed me to 'scale' by growing the number of agents in my organization that I can rely on to assist or work with on a referral basis that extends way beyond the Washington DC metro area. 

@Zackarias AitchisonI rely on very simple elements when assessing a potential buy and hold investment.What would be my all in costs to stabilize the building? 

Hello- I’ve been trying to find the best process/software for market comps and have not found anything I can rely on.