Yeah, I think it is.   I'd recommend saving those.  I think they'll be collector's items one day.

Is it a bad sign when your teams start to feel more like an obligation than anything resembling fun?

Yep.  It's called "burnout'.   That's why I settled on 4 as my magic number(really 3 1/2 so I don't do much with the minor league levels with no true prospects).   When I had more, it seemed like a job.  I imagine the time will come when I'm running 2-3 and looking for a better fit in another world.  I'd say "Set your line-ups and take a few days off" but I know you had a few days off recently.  I'd start cutting back teams.   Less teams are less of an obligation.  Maybe even give up commissioner of one of those worlds.  Being a commish is more troublesome than being an owner.

When I'm setting my lineups, I tend to give more playing time to a guy that is hitting well over the season -compared to a guy who has better ratings and has hit well in previous seasons.    Am I wrong in doing this?

Depends on who you ask.   If two players have identical secondary ratings, it's probably wise to go with the one who has the higher core ratings despite results.  IOW, 80/80/80/80/80 is better than 78/80/74/72/58.  But, if the secondary ratings(speed, baserunning, push/pull, bunt) are different and you're getting better results with the "lesser" hitter, I think it's almost stupid to insist on playing the "better" hitter.

What was the dumbest thing you've ever done?

First marriage. It was less about wanting to be married and more about thinking I needed to sh*t or get off the pot.   We hadn't discussed it, she wasn't really pushing for it(she said I didn't seem like I was in any big hurry to get married) and nobody was pregnant. 

what's the dumbest thing you've ever done as far as the hbd game?

Excluding dumbass FA signings(too many to count), I thought Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: Sammy Mota was going to be the Sammy Sosa of HBD in S1 of Aaron.   As you can see, he got 137 career BL AB.  All courtesy of me.

Early in Avril Lavigne's career, I thought she had the potential to grow up and be a really tight **** kicking rock and roller.
It appears that I was completely wrong.

Was I dumb (in this instance), or was the seed there and it just went horribly wrong?

Hehehe.  I can't stop laughing because you listened to Avril Lavigne.   That's funny.   But, beyond that, I'm not sure there's ever going to be another really tight **** kicking rock and roller.    It's has to be a "ME!!! ME!!! ME!!!" attitude or something.  They just don't have any staying power.  While I still buy CDs, the most recently recorded was Revelations by Audioslave.   That was 2006(I think). 

4 daughters. Shut it.

Really? Do you not think the next great rock and roll revolution is about to happen?
Past ones (as defined by me)
1954 - Rock around the Clock, Bill Haley starts riots
1964 - British invasion
1977 - Punk rock, Sex Pistols explode on the scene
1992 - Nirvana explodes, grunge hits the scene
2001 - White Stripes, minimalist garage rock

...are we not due for the next big cleansing?

What do you think of the Foo Fighters?