I have done cash for keys many times. 

So, as you can see by not wasting time on all 100 people who initially reach out I can focus only on those taking further action to show their interest. 

Hopefully someone with tax accounting knowledge can jump in here with more detailed analysis, but I looked at this a bit several years ago...1) You still have to pay the depreciation recapture on the sale decreasing the net benefit of this approach due to the large tax payment in the 'sale' year2) The LLC would need to not be a passthrough entity so that it can be taxed separately from you, so you have to add another tax return cost for the years going ahead3) Taxing it separately from you likely means corporate status and corp. taxation rates which are higher than yours and I've heard many times over the years to avoid titling real property as a corp...Overall from what I've seen this only makes sense in a select few scenarios, which for most people aren't in play. 

Hiking trails are so crowded that the most popular ones are one-way and you can find yourself waiting a long time to get through some spots on those trails.

Office space is gutsy at this time with many companies working remotely, maybe part of your investment was to bet that people will be coming back to work in person.  

You can be proud of what you have achieved in a short amount of time, this is really impressive!

I have said it before and I will say it again, my wife’s friend said it best when she said “The last time I trusted someone, I had twins.” 

We work with people in your shoes all the time. 

Would love to hear from folks who've been through the process—what worked, what didn't, and what you'd do differently next time.

I had a mentor who stressed "you make your money when you buy"; the next place you get, be sure to haggle big time - and walk away if the price is not low enough.