Lets say 2 people can receive on 2 repeaters equally, but one hits a repeater transmitting better and the other person hits the other repeater better. Am I allowed to transmit on one repeater, and receive on another and my buddy does opposite?
As long as you are both operating according to your license there is no technical or legal reason why you couldn't, but more on this at the end. At minimum it may be very confusing to other users of the repeaters and repeaters are individually owned and operated - you should make sure your specific use of the repeaters in this manner is acceptable to the individuals or clubs that operate them.
As far as whether your license permits it, in the US the rule is "Each station licensee and each control operator must cooperate in selecting transmitting channels and in making the most effective use of the amateur service frequencies. (FCC Part 97.101(b))" and this is generally the same around the world. The spectrum granted for your use is a shared medium, and using more than what is necessary for a communication may be breaking the spirit of this rule.
Keep in mind that when you're tying up a single repeater, you're actually using two channels. Your friend is tying up two channels as well. So effectively your conversation is eating up four channels, during which time no one else can use them. Using two repeaters to hold a single conversation is very excessive, and should only be done when necessary.
Using two repeaters for rag chewing is likely to annoy other operators in the area also interested in using the repeaters.
No legal reason why not as long as your licence conditions allow it. It would be just like linking two or more repeaters together with Echolink or AllStar.
You can do it, but a repeater that hears well but doesn't transmit well is called a rabbit. A repeater that talks well but doesn't hear well is called an alligator. Repeater owners go to great lengths to tune their repeaters to be equal to both transmitting and receiving. Repeater owners that have a rabbit should increase the transmit power. Alligators should reduce power to properly balance the repeater.