Seeing how the GC approached looking at the property did give me confidence.

Going forward, I think all we can do is to make sure that we make ourselves confident with tenants through background check process.

And I know that a toilet paper holder is something sooo miniscule but it boosted my confidence a tiny bit and gave me a small nugget of knowledge I did not have before and I will take that any day. 

If you're intending to use OPM, you will need to build credibility and confidence - the best way I've found this to work is to learn and follow closely  from those doing exactly what you want to do.  

I reached out to the lawyer that set up the trust, and this was his response,"From a taxable perspective, I can tell you with confidence that [wife], as beneficiary of the trust, will receive a step-up in basis for both properties upon the death of her mother.

I know it will be cheaper to do it myself, but I don't have the confidence that I can pull this off efficiently and I need to make as few mistakes as possible. 

Look into things like sales training or something that will help you build the skills to talk to people you dont know with confidence. 

I would try to find a market with solid fundamentals that is either near where you live, easy to travel to, or somewhere that you plan to visit anyway.

YOU NEVER HAVE TO PAY TO TRAVEL AGAIN!

There are a lot of markets here that may be options (may) such as Salt Lake City, Hurricane (capture travelers to the national parks), Garden City (aka Bear Lake) or more expensive markets like Moab or Washington County (St.George).