After a couple reps, I had the confidence to raise money and bring in investors. 

Generally speaking, you need to disclose EVERYTHING in your Airbnb listing because when people lodge a complaint about something, the Airbnb rep will look to see if it was disclosed and if it wasn't, 9/10 they're going to refund the guest without consulting you.

I am currently a Sales rep that drives long hours during the day from customer to customer.

None of these conversations should be the listing broker, and if the market is big enough to have investment sales brokers AND tenant rep brokers, talk to the tenant rep brokers.  

Having a property management business or being a real estate agent may help you qualify for Real Estate Professional Status (REPS) but it isn't a requirement. ...

You do not need to have REPS status to qualify, but it is typically helpful.Here's an FAQ on cost segregation studies that you may find helpful.

It's an ALE rep relationship game that takes months to contact3.

They have a bad rep and require a lot of work but you will always meet some people who made a killing. 

I would strongly recommend looking into either short term rentals (since we can use the short-term rental loophole to reduce your tax liability) or multifamily out of state and find a way to qualify for REPS.

I am not sure about your situation (REPs, tax bracket, age or holding period of the property) but I look at the cost benefit just like an NPV analysis.