I want to move forward with the purchase because it is a great deal on paper but I don't want to do my agent dirty either.

Then calculate when you will need that roof and how much it will cost when you do.I do like that high appreciation potential, and this may work well for you.

I suspect a legal, permitted garage conversion ADU will cost ~6 times your estimate if hands off and probably at least 4 times your estimate if you do the finishes yourself.  

From my point of view for event guest screening and security deposits, Superhog is reliable and integrates well for STRs and events, but you might need to adjust its setup for your use case.

Is it fixed? 

Then what I would likely do is use self leveling concrete to make the surface level and flat.

It depends on a variety of factors. 

I don't agree with this exact order but to be honest and fair, there is more than one way to do it right.

Hey Nicholas, I'm just following up with your last post.How did it work out using Ragan Manning? 

If not that than it might just be a demand issue.