I see your point, but calling mid-term rental arbitrage “terrible” overlooks its potential when executed well in the right market.

I am small time though built about 300 homes in the last 7 years or so.. 4 developments and spot lots in Charleston sc and  Ocala FLA ( Fla was not worth the effort for us)..

And make sure that all items necessary for you to get the best rate possible from your carrier (like 4 point inspections, roof attachment points, pool enclosures etc) are present or available.One nasty little factor that can't be helped is that every time you buy a property for more than than last owner paid - you will have a tax bump due to re-assessment. 

Also in your area that is a little rural if its well and septic makes sure those are checked by professionalsif it has city sewer make sure you do a sewer scope on the line running to the street.. and of course make sure roof is good etc etc.and for sure you can offer what you want to pay.. they may not accept it but its up to you.also ask title company to give you current owner.. and if you want simply make a back up offer in cases the wholesaler cant close this happens a lot and you get a better deal. 

This list is just one of many data points that can help identify areas.This is a 500 ft view, you still have to drill down into neighborhoods, streets and specific houses that will work well as a STR or Vacation rental (not just an airbnb).I look for higher end vacation rental properties above and beyond what people call airbnb's.A room in someone's house can be an "airbnb" after all.I love the new Vrbo commercial with Nick Saban.

I was told to create an S Corp and run all expenses through it and in QB the flips are divided by address into its own "class" as suggested by @Marty Boardman as well. 

I'd avoid doing it on the first or last week of the month as there isn't enough time to let tenants know and PMs are busy enough (as you know) with people moving in and out. 

If this works out well, it can position you to grow your portfolio quickly.

And out of that 5% there aren't really many options that are in solid locations and well taken care of (or at the very least built as multi family).

Then I get STR data from AirDNA to ensure it's well above 1.5x LTR data.