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.

If your tenant left the bedroom with all four walls covered in screw holes, you're looking at costs for both patching and repainting.

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...

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.

If these are the only ways that you can see to make small multifamily work right now then you need to take off your blinders, eye patch, sunglasses, or what else might be impairing your vision.