Gaining

Sounds vaguely familiar.... lol.

I can totally relate. I've "yo-yo-dieted" back & forth for years.. & you're exactly right that you can never really make much progress in either direction - it's frustrating as hell to always reach the same point & then drift back the other direction....

I'm all ears if you find a solution for the "yo-yo syndrome." I've recently started trying to see if I can at least push the envelope a little farther each time, and at some point - I'll have to end up one way or the other... theoretically speaking.

(I'm sure I'll have a cardiac failure right at the most mediocre weight possible... just for the irony).

Anyhow my only "advice" (that I'd not recommend to anyone without deep-seated self-destructive tendencies) would be to work with a trainer when you feel the need to get in shape, and let them decide what outcome you should strive for. Then do the same thing (except the exact opposite) when you get motivated to gain - and let a feeder / encourager decide how fat is fat enough...

(These statements have not been evaluated by any qualified healthcare professional, and are most likely to cause... you get the idea...)

Realistically you need to evaluate your definitions and one of them is going to have to change.
Personally I view Fit as not struggling with mobility, so my workouts will focus more on condition than trying to get thin or buff. This way I can maintain my Fatness without feeling run down or having to worry about being able to keep up with friends when we're out. It lets my biggest worries be about seating and not how out of breath/exhausted I'm getting.

While you may not be able to Qualify for the Boston Marathon at 400, it certainly didn't stop this guy from finishing a marathon.

I consider myself fat. I'm approximately forty pounds overweight for my height, according to the charts and I have a BMI of 31. However, I run everyday or at least five times a week, over a mile. I also do sit-up five times a week(50) and pushups three times a week (50). So I feel I'm in reasonable shape, maybe not marathon shape, but I can run a 5K and not feel like I'm "gonna die". It really is a matter of where you want to be, with mobility, "wind" etc.

Lol, that is definitely not me, I wish I could claim to be a 400 pound sumo wrestler. Last time i ran a mile it was in highschool, and I never had a passing time on it even then.