BUT, can Google or books answer you within hours of your time sensitive question?

My fiancé is applying to medical schools and would start school in the fall of 2025.

While completing a Cost Seg study, they were very resistent to me using 6% and because of time-sensitivity, I decided to default to the "rule of thumb" method that you mentioned and used 80/20. 

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

Here are the Positives:Upfront Payment: The tenant’s offer to pay the full year of rent upfront, along with the deposit, shows a commitment and provides financial security for you in the immediate future.At least She was Honest in Her Communication: The tenant has been transparent about her situation, which can be a positive sign of reliability and sincerity.My Negative Concerns:Her Future Financial Stability: It's only a one-year lease, if her medical condition and financial condition should worsen (Heaven forbid), you may have to face her wanting out of the lease earlier than the 12 months and eventually you may be faced with having to decide not to renew the lease (after her 1 year contract is expired) based upon the sad news of her condition becoming worse, (Heaven forbid).  

The price per sqft is very high for an office built out for medical use.. however, there is an in place tenant paying strong rent with 3% increases for 10 years (close to 7% cap, NNN)What I don't understand is why the tenant agreed to pay close to 2X market comps in rent in price per sqft per year for this facility.

Airbnb will prohibit sensitive information like if they shared their phone number or email but I’ve had other hosts ask me of my full name and then they found me on Facebook and connected with me that way. 

It depends on how price sensitive your market is  Also, you said there is a lot of competition.

USPS contract workers building a robot to sort mail, Travel Nurses, Professionals relocating, A medical group rotating out their new surgical Dr. residents for training in jax  :) A husband of 33 years that got pushed out by his wife - hoping to go back.. but he is still renting from us ...yikes - no judgment! 

Medical costs....