Are there any good deals to be had for The Simpsons season sets? Is black friday the only time they seem to drop to $9.99 or anything reasonable?

Funny you should mention this as The Simpsons had almost totally slipped out of my mind. S13 and S20 on BD (for about $10.50 each after coupon at FoxConnect) last BF was my last Simpsons purchase. Since then I think they came out with another season, but I haven' seen any deals on it. So I think the answer is: yes, wait for BF to make your Simpsons purchases. Since Fox is so slow at releasing them, you pretty much have to wait a year between sets anyway, and BF seems to be the only time they go on sale. FoxConnect deals are the best if they have them like previous years.

It's sad but true that I used to love The Simpsons, but somewhere in the teen seasons they started getting less and less funny to the point where I just stopped caring about watching them and told myself that I'd buy all the seasons when they got cheap enough and watch them then. The series devolved into "Homer becomes _____ (insert occupation), does stupid stuff, and in the end everything returns to normal". Mr. Burns sure loves that yellow guy in sector 7G because he keeps getting his job back. The episodes seemed to have become designed around pop-culture reference parodies rather than coming up with a funny story/situation first as they did in the old days.

I'm not disagreeing with you, but after twenty-some years, I think they've pretty much run out of new funny situations... I love that South Park episode where Butters is trying to think of plotlines, but "SIMPSONS DID IT!" And it's so true...
I don't even watch the show regularly anymore, and with the exception of season 1, I haven't even been watching my Simpsons collection. I own all of them except for the last release, and I don't plan on buying anymore, unless of course I can't resist the BD price (like last year at Foxconnect)

Which were funny when I used to know what hell they were referring to!

Simpsons season 14 was $12.99! Now it's back up to $19.99. That will teach me to ignor my Camel Camel Camel alert for a day.

I like seeing something in pop culture and then thinking that in 3-5 years, long after it's gone, The Simpsons will finally get around to making a joke about it.