I'd start by trying to find the single reward seat now. Use the calendar to find dates. If the dates work, try searching for an upgradable flight on the same dates. Repeat until you can find a pair that works. Book them. That's all there is to it.

And you have a 24-hour cancel policy that works in your favor to try to get on the same flight.

That's the good news.

The bad news is that CO has switched to a 764/762 combo for FCO service for next May, so the BF capacity is lower than it is this year. That will work against you. Plus CO doesn't release inventory in the front cabin this early, so you'll have to keep watching that. As for the H+$100 or lower fare + higher copay, check the prices and figure out which makes more sense. Sounds like you will be going for the H to get the EQMs, but make sure that you're not paying too much for them.