I noted the year-over-year increase in STR permits, the decrease in average nightly revenue, and the sentiment that economically-incentivized sellers would flood the market after this winter season (effectively increasing housing supply and decreasing prices).

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. 

MTRs are a lot about location and proximity to businesses that bring in workers for these types of stays. 

Landscaping pay $100 to local handyman type workers who do a good job.

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

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.

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

If you will be doing future deals with your co-worker you might consider forming an LLC or partnership.

How would you pull permits if you can't do so yourself?  

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