Here's a "trick" we used to do back when I was prototyping air cleaners at Canadian Fram. Get some plasticine (any color will do!!) roll it into sticks about 2" long. You'll need a few to get the entire area covered. Place the sticks on top of your existing air cleaner, hopefully and original, pressing them down so they hold in place. I'm sure you get the idea. Once positioned, shut the hood firmly. Open the hood and measure the height of the sticks afterward. That is your clearance between hood (and plenum) and cleaner cover. That is the dimension you need when the Windsor is in. A spacer could be used under carb if it needs to come up, or a thinner one to lower it. Frame mounts may also play into this, then it might snowball into drive line angles etc. etc. That's not an area I have experience, but my senses tell me it could be so.
Best bet, go buy a Cleveland and loose the possible issues.