Hey Abel would appreciate that info as well as I also wholesale in long island!

My wife and I are starting our investment journey and have our heart set on Anna Maria Island for our first STR/BRRRR.

The big island has a lot of preforeclosures, vacants, and land.  

Hello~ I’m operating on the barrier island on the Space Coast of Florida and have found homes to buy, and I have a friend in Cocoa who has been buying condo units in the same building, so very much like apartments.  

and I know there is some form of cancellation but not this close to the stay and If I could i would postpone 2 days so the first day of fishing is not in snow flurries :)the other major issue for me is POINTS  i earn enough points each year to get 10 to 14 free nights .. like in Puket  or last fall in Lisbon or a few years ago the Hilton Wikaloa on the big island and they upgraded us to a suit that was easily a 7 to 8k perk all for free.  

I do have a resource on island who can assist you. 

For example, https://normanlykes.com/ Is yours a potential luxury home on a multi acre estate or on an island?

For decades Detroit has been an island to itself.

I do not see anything in your post making the apartment "uninhabitable."

Without diving deep on numbers, places like Wisconsin Dells and surrounding areas, Munising, MI for Pictured Rocks National Lakeshore, anything near Mackinaw Island - Cheboygan and Saint Ignace, lake towns near Boyne/Boyne Mountain to get some summer and winter traffic, maybe something near Arcadia Bluffs that sleeps 10-12 to host larger groups coming on a golf trip.