Once dried out in a day or so, we send out a vendor to replace, patch, paint the ceiling where it is damaged.

This is because it was poorly converted, improperly done, "patched up" over time, and might have mixed up mechanicals etc.

I remember when my buddy Mike went through a rough patch..divorce, bad investments, you name it.

This is because it was poorly converted, improperly done, "patched up" over time, and might have mixed up mechanicals etc.

I'm thinking of a short term vacation rental (that'll just be about patching up a family property that happens to be in a heavily touristic area) and then in the future...

Quote from @Jackie Liu: Hire someone to patch and paint the walls, then charge the tenant whatever that costs. 

I am unfamiliar with how long bond lasts, how sturdy it is over time, and will I be replacing this door jamb in 6 months even with a patch job done like this because it will look the same way and all wear down? 

From what I've seen through pictures, the quality is sub-par (e.g. bad patching, no primer used, no corner bead used, etc.).I have recently started to get more strict on timelines (this is now 2mo delayed), and now he is halting the work.

We are still waiting on rent checks to be shown on the dashboard, there has been a rent dispute with the current tenant and the prior owner (not 365's fault but still has not been settled), and one other issue for something that needed to be patched up. 

FWIW, I heard the same thing about Patch of Land too.