When you don't have a two year tax history of rental activity, the lender will usually accept an executed lease then use 75% of the lease income and 100% of your recurring expenses in the DTI calculations.

I think you're right on the money when it comes to building that review pool and/or recurring tenant base (even for less income at the beginning) and have slow easy-to-digest nightly rate increases as time goes on.  

Is this a one time $8k, or this $8k a recurring event 

These are things that I did that helped me ease my anxiety and got me ready to start:- Visit as many properties as possible to get comfortable with them and understanding what is on the market and what you could look for.

I’d maybe get a second est just as a gut check, I usually get 2 estimates for things this size unless I’m working with someone I have an established/recurring relationship with and trust.  

I know someone who has a "service animal" (so she calls it) for her anxiety.

What's the best way to automatically debit a tenants rent and have that recurring monthly?

I have anxiety just from reading their posts.

I also have an investment account through Wealthfront (robo investing platform) and have a monthly recurring deposit set up.

I’ve noticed a recurring theme with starting out is just making connections.