What other steps would you take to see if it makes sense to relax the rental criteria?

Communicate with your tenant on tasks you are uncertain about and confirm if there are comfortable living with fixes you completed or if they would like a professional.

Then start analyzing deals so you get comfortable with that process.

I’ve visited every other property I’ve considered in the past, so this is uncharted territory for me, and it feels a little out of my comfort zone.I’m considering putting it under contract sight unseen to lock it up, but I don’t want to make a rookie mistake here.I'm looking for some advice here.

The question is mostly a personal financial planning question and it depends on your preference and what balance of risk and access you'd like and would be comfortable with.

Get out of your comfort zone.

I would suggest getting another full-time job for the time being and investing/doing STR on the side until you can fully and comfortably replace the income that you would be receiving from your job.Is your LTR in need of repair?

How comfortable are you with the idea of trusting agents to lead showings versus allowing prospective tenants to tour properties on their own? 

Our offices are in the southern parts of the US so naturally we're more comfortable with buying in our backyard.

I'm curious if you'd feel comfortable PMing me how your tenants do it and if there's simple deterrents.