I understand each city/county may have their own permitting requirements, fees, regulations, etc. but I'm wondering how people are making any return on their investment if it maxes out at 90 day rental.

You could also consider selling one property, like the condo, to reduce management burdens and free up capital for reinvestment or debt reduction.

I live in California but looking to invest in Lehigh Acres with a new build Duplex.

If a property appreciates at 3%, it is on the entire property, not just the cash invested.

Hi Everyone, I hope you are enjoying the long weekend, I am from Regina, SK, And fairly new to Real Estate Investing.

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

There is a syndication in which my wife and I would like to invest alongside with another couple. 

He could then write off that basis if the investment went to zero 

I was in a similar situation when I wanted to start investing but didn't have a primary yet and lived in unaffordable Denver...I ended up investing out of state.

It doesn't perform well; your neighbor is a nightmare, they put more regulations, you get tired of running it etc.It may not be your first choice, but it will be a smarter investment overall, especially for newer STR investors.