Starting to consider whether to convert one of my LTRs to an STR. I'm already familiar with some of the basics of how the markets differ, but I'd be curious to hear what some of you have experienced in regard to any ...

What is their incentive to pay the rent at a location they are not living in?

One of the biggest risks I observe with flips and first time investors are instances where the project goes over budget or gets stuck in mud, can't sell and even worse the borrower doesn't have the credit profile to refinance out to a lower interest lending source if borrower is required to hold the property as a rental. 

Sounds like you are on the right track in offering incentives. 

This is an incentive to do your Roth conversion this December if you decided to convert.Backdoor/Mega Roth contribution.

I've been doing investment real estate for many years and the biggest way to get started is finding a commercial real estate market you can afford as the biggest hurdle.

Sometimes they’ve got resources or connections that could help speed things up.What’s your biggest concern going into the hearing?

Finding the private money seemed to be the biggest challenge my friend has had while doing this. 

Biggest caveat is you didn't mention the location.

I have always been interested in home construction techniques that are different or older.Container homes, these sorts of shot-crete homes, bale homes etc.The biggest issue is not that fact that they will rent, for if they are in the right location, of course they will rent just fine.