It ain't easy to fully setup and furnish a STR from a long distance.

Due to Engelo's team and contact I was able to secure everything from a distance (CPA for taxes, Lawyer for the setup of the LLC, Insurance, inspection etc etc..). 

I think the latter would have to be walking distance to the stadium $$$. 

So I trade risk related to out-of-state investment, with risk to hold huge leverage in over-bloated market in tenet friendly state, but I am losing opportunity to build a skill-set of out-of-state investing which will help me to scale faster and be flexible in the future.If we buy cheaper house but further from the city, we will spend a lot more time in the commute(3 days in the office mandate), in this case we will trade time(commute) for money(affordability) it makes it not an investment, but another work.

It's crucial, however, to consider managing a long-distance property, especially regarding selecting reliable tenants and handling maintenance issues.

I still haven't bought my first rental yet, hoping for something driving distance from me (West Linn).

Primarily interested in long distance markets due to prices in my area (San Diego/California).At a stage where I am evaluating my savings versus the upfront costs to get into a STR property.

I recently became interested in REI after I found out one of my bosses at work has been doing long distance investing in multi family homes. 

I commuted to work on it a bunch of times and "fake pedaled" the whole way. 

I also wanted to add this book from David Greene for long distance real estate investing given that your focus is on mulifamily properties in both CT and FL:Long-Distance Real Estate Investing | Out-of-State Investing Book – BiggerPockets Bookstore