KSH, dearest KSH!

If you are riding 3-4 times a week and training for tris, you must be pretty fit, and who cares if you weight more than you've ever weighted. Although you don't seem to think so, you certainly look fit, too. We're so tough on ourselves, needlessly so. You definitely don't need to put yourself down.

Getting some outdoorsy pictures also sounds like a great idea to me.

Another thing: I have had the chance to work with professional photographers (taking pictures of me) a few times in my life. It's always been great, and the results were always impressive, even when I didn't have the best opinion of my looks at a given time. They know how to get a flattering angle, that's their job. Your job is to SMILE.