Talk to lender to find out how to transfer assets without triggering due on sale clause.Did I get all that right?

Downside is you likely need to be asset class and location agnostic.

It depends on your goals, I would say outsource the management & hold the asset as nobody has regretted owning real estate on a long term basis. 

The typical clients that seek out cost segregation studies include:Real estate companies that buy and sell multiple properties each year.Individuals with a portfolio containing investment properties including apartment buildings, multi-family homes and even single residences.Franchise owners with properties that are similar to one another such as assisted living facilities, storage facilities and golf courses.Business owners of hotels, food facilities, shopping centers, restaurants or manufacturing plants.It depends on the type of property, but generally 15-45% of the building’s costs can be classified into assets with a shorter life.

Even if you do not mess up any steps in this lengthy process, you are looking at AT LEAST 90 days before you get your asset back. 

The problem in analyzing is we have no idea what Thomas' personal FICO/credit history, assets, vesting type etc.. 

Same for fixed assets.  

I changed my strategy from 2 years ago of acquiring more doors and "cash flow" to now looking at the asset if I continue to buy. 

But assuming its a stable but growing market, every dollar of Net Operating Income you are able to force is explosive to the underlying asset value.Under both of these scenarios, you do not need to syndicate as long as you don't go too big on the deal size. 

I think the shift toward risk-on assets is lowering demand for safer investments like T-Bills, especially as investors look to outrun inflation beyond what CPI numbers reflect.