I'm replaying S+M after some time on the shelf... with all the dialog branches it has a lot of reply value if you ar eno longer worried you'll screw up the game. (not that afaik there is any way to actually screw up a TTG game - i.e. make it "unwinable")
305 wrapped everything up nicely. It's the end of the series with no cliffhangers left (well not major ones anyway... Sibyl's baby and superball's employers are really all that's left to explain...) My best hope is that they'll do a 10-year anniversary special and release a new game/season then. But, as somone above said, I think they retired the series to shift to more serious games. S+M was great for getting TTG known, now that they're popular enough to get big-name titles, I suspect this will be relegated to the back of the proverbial shelf much like "HtR2" was...