I'd love to utilize their expertise when assessing a property since they are local but I'm not sure what the general expectation is when I don't have a tangible property and I have not entered into contract to work with them yet.Some questions I have are: local regulations/permitting timeline, property's potential from their perspective, landscaping/amenities cost estimate (they also help facilitate this).

This approach conveys your respect and appreciation while making it clear that your decision isn’t personal—it’s practical.

You have to practice and find smart ways to move around PPC/PPL is definitely something I’m keeping on my radar, it’s great to hear that it's working for you and bringing in motivated sellers.

I am currently researching the different regulations in Ontario and GTA.

Oh, and the platforms are actually more friendly to the buyers than sellers. that is why they will take money from hosts on practically any complaint from a guest, or suspend a persons listing until they can prove/disprove any guest allegation.

Why who opens doors should be regulated is dubious, but it is in most states.

Best practices for security deposit deductions (damages)?

The sellers have not been responsive when asked to provide that information, which is why I was wondering if it's a typical practice prior to submitting an offer. 

As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

Anyone have practical experience with this that we can discuss further?