You need to buy or borrow a couple of different windage trays to see what works. The Milodon stroker one is super deep and I've never run into a combination that actually needed it. I use the standard Milodon windage tray with 4.25 stroke and 2.20 rod journals. There are a couple of other windage trays on the market so you can mix and match until you find one that fits.

You'll need to decide on oil pickup before you figure out the windage tray though since those things rarely play well with each other on a stroker.

I'd highly recommend staying with an internal pickup. Do you know what pan you're going to use? For a street car I'd stay with the factory Hemi pan. For heavy duty street use and some track time I'd use a Milodon road race pan if it fits for you. It is expensive but it should fit in your car and it will work really well without hanging down low. The external systems are expensive and a hassle.