You’ll definitely want to dig into the zoning and permit requirements for your area to get a clear picture of what's allowed and what the associated costs might be.Also, don’t forget to factor in things like parking and whether you’d need to add a kitchenette to make it a viable short-term rental (STR).

Many cities in the NW will require a permit to cut those down I know where I live you cannot cut a tree without a permit and you need to get an arborist to write a report that the tree is a danger. from what i see I dont  think the arborist would need to go on the other property to do a report but leaners can stay that way for years and years. 

One that has strict STR permitting with exceptions for owner occupants would be a bonus.

Even though the house next door was able to get a permit for a sober recovery center doesn't mean you will be able to get one.

When you apply for a rental license do they look for un-permitted work?

Our bids ranged from $10k to $25k for the same scope of work with permits.  

Is it worth getting a permit and setting up a vending machine in a multifamily, with 10 or more units? 

Oh and dont think about STR's...Charlottesville, Waynesboro, Staunton, and Harrisonburg have been denying permits due to affordable long term rentals. 

Both require a postal permit so the saving is gobbled up fast.  

As someone who recently completed my first fix-and-flip project, I can share a few challenges that took me by surprise:Navigating the local permitting process was more complex and time-consuming than I anticipated.