It may sound easy and simplistic but itś so much to it.  

Anyone have any ideas on how to find relatively inexpensive programmers for what even I would consider to be a simplistic scraping program?

In reality, your question is too general and simplistic.

You seem to gain negligible benefit from doing so unless you file that out of state LLC in FL (in my simplistic view of things this makes your WY LLC also a FL LLC).What I intend to do is have in state (single member) LLC hold the title with that member being the WY (holding) LLC.

It is scary how readily newbies ask questions fraught with peril and how quickly some questionables here spoon out simplistic, one size fits all answers.Do they even know what country/state/judiciary the questioner is in?? 

Making this simplistic.

I asked for proof of history of rent paid and the seller responded by saying he doesn't have rental records because the renters deposit rent to his account (using that simplistic language).

There are lots of variables but that’s the most simplistic.

(And I mean cash reserves in place *in addition* to the down payment for the next property.)The above might be a little simplistic; and even very conservative hold investors can take hard hits.

Your knowledge base is obviously extremely limited, so you MUST keep strategy equally as limited and simplistic or your gonna incur education via pain.