Washington state’s capital gains tax, passed in 2021, imposes a 7% tax on any gains of more than $250,000 from the sale of stocks and bonds, with some exceptions.

They didn’t go as strict as they threatened, at least not yet…https://www.atlantaga.gov/government/departments/city-planni...2 properties maximum and the first one must be  your primary home… so be prepared to move there and pay state income taxes  https://www.atlantaga.gov/home/showpublisheddocument/54610/6...you and your landlord will have to get this form notarized.Please just make sure you have a plan to keep making rent payments after your short term rental plans are banned.  

I don't know the cost of things in your area but you would get the proceeds of the sale tax free from federal income tax from the primary residence exclusion.

Having one asset per LLC will drive you and your accountant insane and when you realize they charge like $1000 min for LLC returns and you have 5 LLCs that the $5k tax will eats up 1/2 your cash flow you will be like oh boy…

At today's rates I'm not sure it would cashflow by the time you add taxes, insurance, r&m reserves, etc.The average rate today on a 30-Year fixed is 7.38%. 

Now, you still could do a 1031 exchange out of Puerto Rico and into a property in any other foreign location, such as Mexico.  

When I first considered buying in the US I considered North Chicago as I know and like it but I'm aware of the high property taxes and question the longevity of the market there with a declining population and all that.I live overseas currently so any purchase will be remote for me and I will get it managed, I may never even see the place so I'm quite open to where I could buy.I wanted some thoughts on the best places to invest?

My wife is currently studying for her real estate license, so we can perform a cost segregation study on the property when we buy one to reduce our tax burden for 2024.

By building a seller credit into your offer, the seller can pay for ALL of your closing costs and prepaids, and you will get your earnest money back, plus any property tax proration credit as applicable.

Because of the protections an LLC offers in this space, I'd simply say my non-expert opinion would be to spend a little extra to make a separate LLC for this new home, for the legal protections & to make your taxes less of a headache for you.