Also keep in mind the experienced investor will have tons of relationships in place that you will be able to leverage that will save you 10,000's in time, money, and trial and error.

Many years of trial and error have made that possible, however.

Then tell her you are coming such and such day just to trial it.

A wraparound mortgage  - This is a variation of a seller second mortgage wherein  the seller remains obligated to pay the underlying first mortgage and continues to make payments on the first mortgage loan,and the buyer makes payments to the seller on a new mortgage loan that is subordinate to, and wraps around, the first mortgage.

"It'll just come visit one weekend a month" "It's not a pit it's a Staffordshire Terrier""He's the sweetest dog ever, crate trained, doesn't chew" (and variations of this, over and over)@Joel Owens it's a cultural statement and a pride thing.  

Are these people finding great deals, or do smaller markets and economies allow for rule variation?

I think the trial by fire approach to RE is sometimes inevitable, and is necessary provided each lesson is learned only once.

I paid for it on my credit card and then before the end of the "trial" I cancelled.  

We also follow a procedure similar to the one articulated by @Jon Holdman with the variation that we credit the application fee towards the security deposit of the successful applicant.

I don't mind getting dirty and I've learned so far that the best way to learn by is trial and error, but I'm here hoping to pick up tips and advice that can save me some strife.