Any person ever worked with Paul Argueta (Dispodragons) or Alex Martinez (Real Estate Skills) as a mentor/coach, what has your experience been like?

I did a one-year personal coaching with RichDad in 2008.

It's a personal preference.

I have not personally tried the Wire feature though.I am an Accountant and use it and refer my clients to it as well, connect with me and I will look to see what the costs are to send a wire, they do allow free check and ACH payments if timing is not a factor.I had a client who used Titan, and as an Accountant I did not like it.

Instead of being discouraged by a property that doesn’t quite meet your needs, why not see it as a chance to personalize and add value right from the start?

Personal use - if you or your family used the property for personal purposes, you will need this to factored in. 

Assuming I also use the Airstream for lodging while traveling for personal reasons, would I just take a pro-rated amount of depreciation for the amount of use that is business vs. personal?

There's no way around it unless you specifically work for one person only.

To answer your question directly: a person should apply (whatever that means in your process) before being asked to screen.

I'm thinking I could have someone manage the build as my eyes and ears when I'm working.