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You will want a detailed set of documentation for each of your medical expenses. I use a spreadsheet to collect a master data sheet to track ongoing and past expenses since I opened my HSA.
I also keep scanned copies of my Explanation of Benefits (EOB), Invoice, and payment receipts for each medical expense.
I make no guarantees that this is sufficient documentation. Consult a tax lawyer or CPA.
Have a cash buffer of at least 1 full year of "maximum out of pocket expenses" as defined by your health insurance plan before investing your HSA savings.
This cash buffer allows you to weather any volatility in the portfolio.
An even better buffer would be 2 full years of "maximum out of pocket expenses" because this prevents the problem of a December injury or illness running into January and maxing out two years worth of health expenses.
Maintain this cash buffer throughout the investing process
A health savings account is the best tax-advantaged account currently available for workers in the United States. Thus, it is important to have a plan and understanding of how to invest your HSA money and maximize the benefits of this unique tax shelter.
