You can easily tag each transaction using categories that synch to your Schedule E for tax time.

Are there any unique considerations or red flags you look for compared to the traditional rental process?

Other months look more normal for this time of year.

As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year. 

What would you say to the first time investor looking to buy, rehab, rent, and refinance in Dallas?

I use a loan servicer who processes the borrowers payment and then sends to me.

With one deal under your belt, financing may also be easier this time.

These people don’t have the time to do it themselves.

Quote from @Michael Addison: Hello,First time out of state investor from CA interested in Cleveland. 

It sounds like you're in a solid position, and taking the time to stabilize before moving on to the next deal is a smart approach.