You certainly want acquire any investments with or through an entity of some sort as opposed to doing so in your personal name. 

Id rather get that sort of person at 1400 then section 8 at 1500. 

I’ve seen two basic suggestions for getting your weeknights filled: longer minimum stays and some sort of pricing advantage (4th night free, lower rates, etc.)What research have you done?

With all the property management softwares/suites/apps these days I'm having a hard time sorting through all the information, so I thought I would beg the question:Which rental property management systems have you all used, and what are your thoughts on them?

I was hoping to get some insight from FL natives on where these sorts of investments would make sense.  

Instead of jumping to a REIT or syndication, you could consider some sort of joint venture.

Find the deal first and then look into doing a hard money loan of some sort.

I am also investing in a REI software tool that will help me do the heavy lifting in sorting and sifting areas I am interested in CT.

Namely for starters, they have professional codes and requirements that force them to pass on investments they would like to buy themselves. 3) I would draw a clearer distinction of sort between "working" and "investing". ;)  Some people just don't have the entrepreneurial spirit or tolerance for risk or etc and thats okay.

I am simply seeking advice to help sort out some conflicting priorities.