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.

What are the benefits of 1 vs the other and when growing your business, which one is better? 

New to the Business, Appreciate Your Insights

Finally, on the business side of things, if I fill my mission to provide a product that is better than the competition or simply not offered by the competition, I shouldn't need to rely on potentially cheap marketing on BP.I understand it'd be silly to not do business if it can be a win-win for all involved but there is the right way to do things and you actually did by contacting me.

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...

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

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

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.