"Should I address my concerns or just HTFU!?"
Do you have a specific goal that you're working towards? If not, you should seriously consider setting one or more. If so, then how are you progressing towards said goal?
What's your age?
Personally, I must have a specific goal and timeline set to put in the kind of dedication and effort that your exhibiting. I can train for Six Gap, cyclocross season, or just to keep up with the fast group on group rides, but I need to have a reason to put in all that work. There also needs to be some benchmark, some way to measure progress towards the end goal.
It sounds like you have made tremendous progress that you can be extremely proud of (50 frigging lbs), but what is it you want? Where do you want to go?