Koyote

With your hands in the drops, there is downward pressure on the bar. This is why handlebars are wrapped from the bottom towards the top -- so that the edges are facing downward in the drops; as you've now done it, your hands will be pushing the tape's edges downward, and hence it won't last as long before getting tatty.

Seriously, go into ANY bike shop on the planet and look at the new bikes -- I can practically guarantee that you will not find a single one with the drops wrapped as in your photos. Nor will you find a single "how to" video that wraps from the hoods downward. So don't kid yourself into believing that you've come up with a superior solution. But it's your bike, and your wrap. Knock yourself out.

btw, I have Shimano shifters on all of my geared bikes, and wrap them from the bottom up, and have never had the issues you're describing. You need to stop worrying about this 'figure eight' stuff and just wrap 'em. I couldn't even tell you how I do it, but it's easy, doesn't interfere with the hoods, and works fine. No bulkiness.