Could be a short weekend workshop, could be a business conference with tons of people or just smaller groups, who is organizing them and where are they going down?

However, if you believe that extends to outside of unique areas like Corktown,  you will find out quickly the reason prices are so cheap.  

As this will be the first time (hopefully not the last ;) I’m looking for a checklist of all the things I need to check, organize & have in place.

There is a gigantic gap between the leads between that certain company and their competitors.SEO results in about 10 times as many organic clicks as they get PAID clicks.Now does ANYONE still dare debating that your FB ads threatens SEO?!

If it's a larger organization, feel free to inquire about their different staff qualifications.2.

You may have the unique advantage to use the current 2 family on the lot as collateral which could increase your LTV.300k to build seems low to me, even if you were going to GC the construction yourself.

Do you post ORGANICALLY on a regular basis.

I can't speak directly to your area, however, I do think people are looking for more unique properties when they vacation. 

They have been perpetually "working on it".Beyond is a significantly inferior tool for pricing my unique properties. 

Earthbound Brewing is on Cherokee Street and very hip/hipster kind of place with unique/funky beers.