First of all, don't feel bad, he just needs some tough love, and luckily you're at witts ends and are ready to give it to him.
Some ideas:
1.) for time out, put him in for 2 mins(his age), set a timer for that long, tell him that until it goes off he can't get up, no talking, no toys, just time out, if he breaks the rules, reset the timer, when he learns it gets him no where, he'll quit trying to get out of it.
2.) hes old enough, make him help you clean up the messes he makes, put clothes away, clean up milk, etc.
3.) Put child locks on the fridge and cabinets or just don'r let him in the kitchen via baby gate.
4.) put your make-up and anything else in the cabinet and put a lock on it.
5.) if he spills his drinks on purpose keep them out of his reach and make him ask you for a drink so you can watch his with his cup, or just put a spill proof lid on extremely tight so he can't get it off.
6.) no food or drink out of the kitchen, the end.
7.) give him productive things to do, color, toys, books, nothing messy though like play-dough.
Good Luck