A good way to get an understanding of how to get into STR is :STRATEGY: Start Up Guide to Short Term Rental Investing 

Table 1-4 is the Rollover Chart in IRS Publication 590 that can guide you.

True investors, that are personally guided, can get good results.

As for your specific scenario, I would encourage you to reach out to a professional to guide your tax planning activities ASAP.  

Luckily I have the help of a good lawyer (@Diogo Capela) who has help guide us through these early days in Portugal.

I think this will help to guide you down the right path. 

Then let them guide you, play devil's advocate and act as the borrower, and cover your blind spots.

Pretty much the core of the STR business.Higher your rank gets, you can increase your price and be more picky in selecting customers which usually lead to a better review / less party or complaints / less expense and higher profit with a happy life.I know some people will argue, but the ranking system is the truth and should be the only guide to your STR journey. 

I host meetups and would be happy to connect you with the right people to guide you through that 1031 process. 

Give The Ultimate Guide to Grading Cleveland Neighborhoods a read to see what's what.