Myswag still owes Brett $5K
To me, at least, that's not acceptable!
I'd suggest that him being repaid (even if slowly) should be a priority, with a small amount coming off the top of every sale - maybe 50c from each sticker, $1 per stubby holder & so on up to $5-10 from each shirt / jacket.
With regard to ongoing costs, is there a single time of year that you'd like to see lump donations come in eg July for tax, or would it be better as a constant trickle year round