It would be good to have another of AIO's "long, humor filled courtships" as you nicely summed them up. And apart from inevitibly priceless, it would be touching to see Wooton, who's normally the always-happy goof lately, be humanized again at times. An excellent post, by the way.
As to you, OF, basically, you object because you don't think they're really in love, and because Penny gets on your nerves. I'm quite sure if Wooton proposes to Penny and she says yes it will kinda be a hint they care for each other. And most fans love Penny, that's why the AIO team is using her so much, so who cares if she bothers you? It's a pity, but it doesn't affect anything.
Froggy, those are some very sweet thoughts. In any case, Wooton would, errrr.... be having some very un-Wootony and grown up moments with Penny. And while that wouldn't necessarily show a whole lot (Eugene is still a very similar person to his pre-Katrina self.) But there would be changes:
http://twistsandturns-aio.weebly.com/the-courtroom.html (scroll down here for some excellent thoughts on how Wooton would change if he married Penny.) But Penny would
certainly change. Very significantly. The entire premise of Penny's personality is that she's a bit unconfident, easily led... in short, very childish and
doesn't know who she is. Once married to Wooton, all this would evolve. Not necessarily go away. But it would have to make itself known in different ways. After all, Penny would now
know who she is: a wife.