I live in the Milwaukee area and want to get started investing locally but eventually want to branch out into other cities and states.

What states/cities make the most sense right now? 

Hey @Isaiah Cortez, here are the deets on STRs via the city - https://www.fortlauderdale.gov/government/departments-a-h/de...I don't have any real insights on the area, but do a search and you will find some details.

I've got a CFO client in Kansas City that has a 40+ unit SFR portfolio and is now targeting 5+ MFs.

As for the area I am thinking of doing my area of San Antonio and nearby cities.

In a dense area, such as in-town (city, dense suburb, etc) you should be able to find sales within a half mile. 

I understand why carriers associate Condo/PUD construction with greater liability risk (I am sure being based in Philadelphia, a jury friendly city doesn't help either) but curious which carriers others are finding to price coverage without this exclusion and also price the coverage competitively.This also serves as a reminder to review the coverage when you hire a GC for more substantial or unique construction assignments. 

The City of South Lake Tahoe does not allow short term rentals.

I go by city actions and not what is written.  

What city is the best market?