I've dieted people down for shows using long esters. I've dieted myself for shows on long esters. All you need to do is use more AI. I would suggest you do some more reading here before you hop on a prop cycle for your first ride. If you have never injected gear, you should see how a long ester cycle treats you first. I've broke this down a bunch of times here, but here are the highlights. Part of it is just logistics. Learning to inject several different muscles will be hard to do. If you do prop, you are going to have to figure that out, all in wk 1. With Test E, you only need to inject 2 times. Next, the pain level can be very high. I know, everyone thinks they are tough. I get it. I felt the same way. It's all fun and games until you take a bad shot and it literally feels like someone hit you with a bat in the quad, leaving you unable to walk or sleep on that side, not to mention train legs. Then 2 days later, time to inject the other quad. Then 2 days later the glute. Ect, ect. Pretty soon, you run out of muscles that aren't inflamed.
As for Winstrol, it dries you out, muscles and joints. If you keep the dose moderate and keep the length of use controlled, you should be fine. Its not just the elbows, it's everywhere. Be careful because dry muscle and joints is more prone to injury. 50mg is the most I would use and I would keep it to the last 4-6 wks.
As for overall cycle length, 10 wks or 12 wks is going to be similar bro. If things are going well, 2 more wks at the end might be a good thing. If you've had enough and gains have slowed at 10 wks, maybe its time to come off. Really though, 2 wks isn't going to make or break someone, Do what makes sense based off of how much gear you have. And HCG is always a good idea