Plus, once I tell one of them, the rest will know anyway unless I cleverly disguise it as if I'm just selling individual trailers until they are all goneKind of reminds me of the story of Walt Disney buying all that land in Central Florida for Disney World under dummy corporations.

Anyone have any thoughts for clever solutions here?

. ;)   Probably like you, being in technology I actually enjoy finding clever technology solutions to those inefficiencies.  

In managing the listing, we respond to inquiries and bookings, set up cleanings/maintenance and make sure they are done properly, track events/busy season and set prices accordingly, do inventory on household items (linens/trash bags/toilet paper/etc) and do the shopping for those items.

I mean you can try plugging in the HOA fees, management fees, insurance, taxes, 100% of utilities, cost to furnish, replacing linens on a more frequent basis that you'd think, etc. and see how it all works out. 

I was hoping for a clever, patronizing description of the bar in the ad, but nothing other than "bar area".

I honestly believe that success is measured not by heights attained, but by obstacles overcome ( I forgot who said that, but know I’m not clever enough to come up with it by myself) Circling back to Warren Buffett, if you ask him who are best investors he knows are, he won’t say himself.

My friend is a farmer and pays rent for 300+ acres of land; I think, the owner must be very clever. 

Furniture and linens wear out. 

Hi Marlen,I went through a real estate education/mentoring program through Clever Investor!