I have a Bachelors degree in graphic design, but I really just want to get into the real estate investing world rather than the graphic arts world.

I would prefer it to be my handyman but if my tenants have someone reputable, all I ask is for them to send me their business card.

You deduct it when you first started using it in your rental business, whichever year it happens to be. 

for certain its just like any business under capitalized business fail at an alarming rate.

The non-profit is designed to keep laws in favor or landlords in MT, and I've had good conversations about tenant issues with representatives there.

I don't say this because I'm a HML, but because I just don't like the risk/liability of holding a rental property in my own name.But again, I'm not in that business...Maybe someone who is can shed some light / give better advice...

I don’t plan on trying to do all of those business ventures on the same parcel of land.

Last but not least, my business partner Chris just mentioned to me this website which it seems to be pretty accurate in terms of market rent. https://www.rentometer.com 

I own a business doing about 20K a month but that won't qualify me for a loan due to the timeframe of my business, and my parent's cosign won't help with their DTI ratio after I purchased this second property.

Historical data, new developmental attractions, business relocation, local policy, etc.