@Cbuydos - You hit on a lot of the elements I have been thinking about, where I would rather invest in a full top-notch sail inventory for a smaller boat than a few sails for a larger boat. We carry 2 jibs and 5 symmetric spinnakers on the 40'er I race on, and have two mains; that adds up quick. A smaller boat is less $ per sail, and potentially less sails, to fully set-up. Building that inventory over time is easier as well. (I'd probably be content with an O25, but it would be a lot easier to get the family out on a 911).
Re: PHRF, there isn't a massive difference in ratings between the Olson 911 at 126/132 for the S/SE and the E32 at 156. The larger regatta with ~150 boats with the PHRF range of 100-150 being broken into 5 different fleets ("big" boats, "small boats", ULDB's, Express 27's, and J/24's). Either way there will be boats to race, but in terms of competition I would be more concerned with the E32 getting lumped in with the ULDB boats around rated around 140-150 for smaller races than the 911 duking it out with the boats in the 105-120 range.
To sum up the thread, it seems like the E32 is still a great option to meet our family-oriented near-term goals, with the ability to casually race beer cans and club races, but it most likely isn't the boat for my competitive itch that will eventually come out.
So, anyone know where I can find a 911 in/near the Bay!
(And does anyone have any intel on the 911 for sale in Olympia, WA? Farther away than desired, especially during a pandemic...)
Thanks to all for the conversation, it's been fun.