I’ve read the Bigger Pockets book on long-distance real estate and am eager to get the ball rolling. 

I would roll one into another as each paid off.

The 500 hours test for material participation test has 0 to do with your W2 job. 

ACM (Asbestos Containing Material) abatement is a tough one because often you won't know (outside pipe insulation & 8x8 tiles which I can spot and point out with no testing).

I'm looking at rolling over ~350k into the replacement property. 

You have to come to the table (a future deal) with funds to get the ball rolling.

It is definitely interesting what is happening and I could some see landlord and real estate applications coming soon if this keeps rolling.

But there are other tests and if planned correctly, you don't need these two tests or even track hours the first year if your participation is substantially all hours.

Hope is the industry gets some relief soon and I can revisit some options to further improve asset revenue through amenities and/or roll into a better rate a lower principle.

Currently the options I'm looking at would all have me keeping employer HSA for ease of payroll deduct but possibly adding other HSAs that aren't for adding contributions, but just for rolling over funds and investing.