Again, you should be able to put this into motion as long as you start a paper trail now, if you haven't done so already; you want accounts from different Tenants covering different instances in writing to show a pattern. 

Are there similar patterns in your neighborhood/will tenants/other prospective buyers care about this also?

Even where there’s a favorable fact pattern as you appear to have, unless there’s insurance involved it’s rarely worth the pursuit.

That seems like it should carry some weight, along with knowing the the traffic patterns of the booking cycle etc. 

However, based on your fact pattern, there will be a period of nonqualified use that will reduce the amount of the exclusion allowed.

However, if you consider the migration patterns from CA/NY whose to say it doesn't start to transition there in the next 7-12 years?

Could be anywhere up to 40%.Step 3 - determine whether there's a pattern of flipping activity or a one-off deal.

That said, given my fact pattern of a condotel- how do I even try to allocate each individual who might be employed by the management company vs the number of units in the building.

If it becomes a pattern of behavior a discussion about when they receive their paychecks etc. may help if a tenant needs the rent paid at a certain date each month.

The value and cash flow is legit but im not familiar with long term growth patterns of the area.