Wow....
I know...kind of a lot of info, huh?

OK, what is your work schedule like? What time of day to you have to workout/train?
I work Mon-Fri, but the hours during the day vary. Morning workouts are a possibility off and on (although I HATE them...). Sneaking out during the day can work, depending on the day, but hard to plan for. After work is good, and I can sneak out early sometimes.

Then, I also work in the evening, but at my scheduling...so I can start evening work later if I want.

So, it all varies. (ETA: the good news is I am on my own...no spouse, no kids, no dog...I can train whenever I can.)

Do you currently ride with a group? If so, are they an A, B, or C level group.
No. I've just always trained alone.

There is a group of people I have ridden with once here in town. They are super friendly, but all are multiple Ironmen finishers (including a Kona qualifier). I could start riding with them (and try to hang as long as I could).
The one time I rode with them, they were taking it SUPER easy to accomodate a guy who just had started chemo. It was a 2 hour lactate fest for me!!

There is a group ride in a town about 1 hour away...I haven't tried it yet. Don't know their level. There is no bike club in my town.