I have read other comments that the properties would be considered “tacked together” but would love to hear from one of the experts on here who might have direct experience with this.  

As this is new territory for me, I'd love some advice on how to navigate and manage this aspect effectively.Thanks in advance for sharing your insights!

However, due to short seasons, and more mild winters, I'm struggling to think even 3-4 years from now that I'd pull anything more than $50K a year in rentals.Bills / property taxes are about $12,000 a year.The thing is, being single, and not really dying to work in this area (small town), I'm feeling rather stuck, as is all the equity.I'm currently not working, but very much want to move back to Chicago, a place I love, and start buying cash flowing properties.I'd suspect I would have about $900,000+ after all is done if it sold at $950K, considering the vast array of other things I've accumulated (wood splitters, machinery, tools, MCM furniture, rugs,).

When I used to live in other states, I often would come across free MLS listing booklets in Shopping centers but I don't see those here.Lastly, i would love to ask questions, learn and progress with seniors here.

All you need is a few busy bodies who want to make trouble and you are effectively banned.In the Florida Keys, all but 2 of the islands allow STR for 28 days or more - how many folks can actually rent for a full month?

Would love to hear the responses.

Although I would love to have a management company, I am not sure we can afford it starting out, so I am hoping to self-manage initially and hoping not to screw things up too much!

Would love to know if you find anything.

I'd love to tap into the knowledge and experiences of this community to not only help them find the perfect spot but to also utilize my home as a rental during the 6 week festival. 

Hi @Jonathan Klemm, I would love to link up!