I am building my HSA for the first time this year. My company gives $2,000 toward my account and I am bringing in an additional $3,500 for a total of $5,500. I chose this number so that I would have at least one max out of pocket if needed. If all goes well, I'd like to build my account to around $10,000 by the end of 2017, and then slow down my contributions a bit until I get $15,000-$20,000 saved up. This would cover the family max OOP ($10K) and have some reserve for when my kids need braces or I decide to get the snip snip or whatever else the future holds.