From simple rules like permits to outright bans so that is a huge risk IMHO.

Miami is still doing well, Fort Myers is adjusting and has lower real estate than 12 months ago, etc..)My simple thought, for what it is worth, is choose a place to live and not invest in:  choose the location you and your family WANT to live in ( because of the schools, taxes, weather, other family there, etc...) and then buy and do real estate there (and get whatever licenses you need once you start third party management).I wish you well!

Personally I’d prefer having all my loans with one entity like my local credit union who doesn’t sell them and just have the payments come out of my account that I already have with them, keeping it as simple as possible. 

I've looked at a few of the sites and will reach out to them. 

Buy a few books, start simple, do your own property managing.

Quote from @Grant Francke: For those with using Buildium for property management software, do you use Buildium's public site or do you use a website you have made and maintain?

There are so many veterans who have carved nice paths in real estate investing all over the site and as guests on podcasts that you can learn from as well.

Read some books, preferably those written prior to 2015 when YouTube gurus started telling everyone how easy it is to buy 17 houses a year with no money down.Investing is pretty simple if you just follow the process investors were using since the beginning of time.

Now the business itself is rather simple. 

I used Hostaway for the last year and the they recently snuck in a 1.8% fee for our direct booking site.