I understand the safest option is to have a lawyer review the lease, but I figured I'd try to answer my beginner questions here and not waste the lawyers time (and my money) on the "for dummies" explanation.Thank you!

Anti-money-laundering laws are largely to blame.  

RentRedi is dealing with MY MONEY! 

You didn't mention having other money available.

The other thing that I would look at is private money too you can get it for cheaper and less pricy as they can make their own terms with their money.  

The Retainer Fee is credited towards whatever they buy from us in the 90 days, so in effect, costs them nothing.Note: we're not doing this to make money, but to avoid the time-wasters.

Since this is the tenant's money, I want the bank calculating and holding everything versus storing balances in my spreadsheet.

Tax free money is huge.I may have 100k of instant equity so I don't care about about tax write offs.

I have no social sphere or contacts family or friends in Oregon (I don’t know anyone besides my fiancée).Goals: continue to have flexible schedule while enjoying what I do (selling real estate) and making good money.

Quote from @Marc Shin: Hello - is it worth spending money on boardgames within an STR?