HELL YES! Seriously, you touch on a lot of things that I mentioned in my long rant I wrote post Resignation. (http://psychedk.livejournal.com/8329.html) You just do it so much more eloquent :P

There are especially two things that has also caught my attention - Wilson says his marriages were so crappy, and he also refers to them (all 3) as being mistakes. Why? Why are they crappy? We're never told. It's not like they are doing something to him. More like he's just not getting the mental/emotional stimulation from them that he needs. He does, however, obviously get that from House.

And I always wondered why Bonnie doesn't say that Wilson's affair was what broke them up. She doesn't mention it at all, but on the other hand she mentions his devotion to House as a factor. That's very telling IMO. She does talk about it like she perceived Wilson's actions as being the affair, and I agree, an emotional affair is as much an affair as a sexual one, so she's probably right in her lament.

And I'm convinced that one of Wilson's wives have to have thought it was a strange friendship indeed, and called Wilson on it. I think you're right that Wilson would get defensive about it and just close up. But as you say, he does admit to having all these affairs, and specifically an affair while with Bonnie, so he must know how he feels. And you pointing out the guilt factor is very accurate. He obviously knows he's blown it big time.

Also, I always found it odd that he seems do be doing nothing whatsoever to solve his situations with his wives. We only see how he is while with Julie, but according to Bonnie it's been the same. Wilson neglecting dinners, Wilson running to House's beg and call, etc. And when Julie ends up having an affair, Wilson acts like it's his fault! And does NOTHING to try to work for his marriage. I always wondered why she has an affair AND kicks HIM out. Seems a little opposite, doesn't it? It would look like Wilson had already given up on the marriage at this point, and Julie having an affair really didn't affect him. Sure, he regrets that he fails at marriage, but not that he and Julie isn't an item anymore. Interesting.

Btw, RSL also says outright that Wilson is attracted to House. Not physically, but mentally, so there's really no doubt it is so.

There's another scene that's blatant flirting from House's part. It's from Daddy's Boy, where House is trying to make Wilson have dinner with him.

Wilson: You’re taking it back.
House: Moooom! How about we talk about this over dinner.
Wilson: Forget dinner, you're gonna kill yourself!
Chase: Nice bike!
House: Thank you. See that's how you do it, compliments, dinner.
Cameron: What do you do with your cane?
House: If he buys me dinner, he'll find out.
[some diagnostics dialogue until the ducklings leave]
House: You'd rather have dinner with your wife?
Wilson: Yes, I would. If she were speaking to me.
House: [smiles] Unlike her, I could make it worth your while. [leers]
Wilson: Fine.

And in Failure to Communicate House calls Wilson "honey." Neither of those times provoke a reaction. Apparently it's satisfying for Wilson to be the center of House's attention like this.

But isn't this odd - in s. 4 it's actually Wilson doing the flirting, and the gay jokes. He's mentioned House naked, made references to him jacking off, not once but twice (Whatever It Takes and Ugly), and made the obvious gay reference in Ugly by saying he was tapping his foot like that senator. It does seem like he's becoming far more outward with these things. As for him being gay, well, I'd say a repressed bisexual, but I certainly believe that his emotional affair could be a physical one, if either one pursued it.