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> Aggressively cut my calories and started going to the gym 5-7 nights a week... about 40 lbs between Feb and July

You consider this a success?

Considering the weight has not returned and I've drastically increased my physical fitness in the process, with an overall 100lbs over a longer term?

Yes. On a statistical and personal level, I am happy with my performance. I didn't think I had it in me, to be brutally honest.