The main thing is to stick with great location and premium properties.

@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.

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.  

-> 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.

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.

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

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?"

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.

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