Jail sounds like work! I barely have time to clean house as it is, no time for their rooms at all.
I had a talk with my boys after a big fight about cleaning their room about 6 months ago. Dirty clothes were no longer my problem. They didn't have clean clothes for school then its their fault. Obviously they also had too many toys, because it was too much work to keep it all clean. We decided to simplify.
I stopped washing my boy's clothes for them and that pretty much solved the dirty clothes problem. The first time my oldest had to wear dirty socks and jeans to school he freaked out. He washes his clothes regularly enough to keep me happy now, I remind them every couple of days and they run up and get the clothes and stick them in the washer and dryer. Both boys 11 and 9 have been doing their laundry for about 6 months now and it really helps them learn life skills I think. They take for granted clean clothes appearing and dirty ones leaving otherwise, I figured they were old enough.
I discovered that folding is too difficult apparently and dressers are EVIL. I got some cheap closet organizers with drawers and double bars with some little pocket shelves in the middle for both boys closets. I removed all the dressers from their rooms. They hang all shirts and pants on hangers (easier they say than folding) and they put underwear, PJs and socks in the wire drawers or baskets on the shelves. I liked it so much I did it in my room too! Makes for more space without the dressers too.
As for toys, I have found that less is more there too. We keep it simple. They don't like cleaning up and they didn't play with most of the stuff anyway so we have given most everything away. Most kids have way too much stuff. They have their video equipment and basics like legos and a few select transformers and robotic toys, remote control cars and an assortment of action figures. We have two sets of cheap plastic drawers found at like dollar general (really cheap bad drawers LOL) and this is where they keep the smaller pieces of toys. The robots and cars are on display on desks, night stands and against the wall etc.
However I did threaten at the same time, both of them and they took me very seriously. I told them if they didn't keep their room relatively clean and clothes picked up every couple of days I would do the following. My boys are very concerned with their "cool" appearance and I give things to charity often so this worked.
I said I would go buy school uniforms with 3 pairs of tan pants, 5 solid color polo shirts, a plain blue hooded sweatshirt jacket and plain brown shoes (they both hate brown). The rest of their clothes would be given to charity. I would then remove all furniture from the room and all window treatments and all toys, put the mattress on the floor and that would be their big empty room. No fancy clothes, no toys, no furniture, no TV, no video games. Just a mattress and the school uniform clothes. Neither of them like that idea at all and for good measure I told them this as I helped them clean their room and removed a 33 gallon trash bag full of old toys to take to goodwill and then removed all their old clothing and stuff that was too small.
If they slip up I simply stick to the grounding, and don't let them do anything like tv or whatever until its all clean.
Good luck.