Thanks for all of your replies and advice. It definitely feels like I'm an in-between setting...
I've been wearing it on the tightest setting and it's been tolerable as long as it's cold. However, on Friday towards the end of the day my arm was slightly more swollen, and it was not comfortable at all: I ended up with really pronounced marks from the metal clasp... So I wore it more loose on Saturday, but it's just too lose, having to constantly fidget with the watch to get it to sit right... I'm inclined to continue to wear it in the tightest setting for a few more days, and see if it gets better or if it continues to be painful.
I'm definitely going to have to look into options, since this strap is definitely not comfortable as it is, and keeping me from enjoying the watch. I'll keep everyone posted, thanks again!