@Jill KellerI personally owned and managed several rental properties, mainly one family, 3-families and been advised by a number of attorneys through the years to forget doing LLC's.

I don't know much about it besides there's a plethora of churches, bars and beaches!

Main thing I would think of if you are targeting families are things like pack and plays, cribs, gamerooms for kids, etc. as well.

While I don't want to focus on doing this as my main source of income (I still mainly want to do fix & flips and contract assignments), I wouldn't mind trying it, just to see if it's something that could work for me.  

A couple thoughts on your question:I tell our STR investors in Colorado that their main goal should be to set up the right way right out of the gate.

-> Regarding the short / long term rentals:- short term: tourism is one of the main sources of income of the country and therefore has lots of potential.

I currently live in San Diego, Ca. but have been looking in the midwest, mainly Iowa, Indiana and Ohio, for properties. 

of the "great photo" examples having calendars that are wiiiiiiide open, with barely a booking on them.Fair enough, I pulled these from first page results of nation wide searches (it was skewed SE for me because I mainly look in those areas) so they obviously rank very high on the algorithm.

PMs are busy - if you email a PM and say "Hey PM, I'm looking at 123 Main St. and I think it will rent for $1500 a month, does that sounds right?"

The main reason is that it is not initially set up for a Real Estate business like other “real estate-specific” accounting software.