The last cycle where rates were on a downward trend started in 1984 and ended in 2021.

Finally, your hunch is correct: when the syndication cycle closes, your past "free lunches" will have to be paid for, aka recapture.Here're some relevant posts from your favorite site:https://www.biggerpockets.com/forums/51/topics/839015-are-sy...https://www.biggerpockets.com/forums/51-tax-legal-issues-con...https://www.biggerpockets.com/blog/real-estate-professional-...  

You are buying at, or close to, the bottom of the market cycle for offices. 

Even though rates are high right now, there is an allure to variable rates every time rates are in a down cycle. 

I think if you're getting 25% - 35% more than LTR rent for a 6 month lease it may be worth it be slightly off cycle.

Prime is currently 7.75% and likely to drop by 1-3% during this fed cut cycle over the next 1-3 years.  

Leasing within the school cycle, parents, and turnovers.

There will always be inefficiencies in the real estate sales cycle because of that human inefficiency in making decisions.

I originally lived in it for a year, while if fixed it up so i only had to put 5% down + closing costs(25,000), and the property has appreciated 8% over the past two years(20,000) but not sure if i should rent it at a loss and structure the lease so i am  in a more favorable leasing cycle, or plan to sell it.

Also, is there any method you know of to shorten the cash cycle?