You might inspect them really really well for hairs, even tiny cotton fibers from like a towel. I don't inspect and lube mine "every dive" - more like every day or two, or if they start to feel like they're binding when you're trying to do the piston action to insert the port extension.
Also check for seams or pits in the o-ring. It's possible you got a badly molded one, or nicked it. Once damaged, they'll never come back.
From your original message, with the dome 'wobbling' on the surface, the O-ring should still NEVER be able to 'come out'. It should be completely trapped, with the angled part of the port extension meeting the inner faces of the port locks perfectly flush, which means the o-ring is entirely trapped between concentric cylindrical surfaces (the outer cylindrical face of the extension, the inner cylindrical face of the housing mold). Any chance your o-ring got 'stretched' so it's not a tight fit over the port extension? Again, if it wasn't lubed and was tight on the very first insertion and bound up a little bit, it could have been stretched, and won't necessarily recover.
I wouldn't say you're the "only one" having problems - don't want to make it sound like we're all blaming you. I have heard others say (it seems to be a mantra, frankly) that Ike is somehow less reliable than other ports, although I really think it's probably more a matter sample size (many more Ike housings than more expensive housings in use, and across a broader range of users in terms of experience level, hence...statistically there must be more failures). [EDIT - just to clarify, by this I mean with a larger # of housings, and the exact same failure rate, statistics says you should have a larger failure count. Not larger proportion - just same small percentage of bigger pool will mean bigger numbers. Factor in the less expensive factor and the sheer quantity of Point and Shoot housings they make and there's also a skew toward perhaps less overall careful users (not aimed at the original poster here at all). Although admittedly most of the point-n-shoot housings don't have the port seal in question.... I'm an Ike user myself -- past and current -- and have never had a leak, although I have at times criticized the 2-port system on this very site. I just don't want to leave the impression I'm bashing them as that's not at all my intent.]
Clearly port o-rings are a source of failure (on any housing) and Ike responded to at least the psychological fear of the older 2-lock system by beefing it up. But your description really does not sound normal.
Can you take pictures of your port extension with o-ring and locks engaged, just in the air, and post them? Would like to see how it compares to how I think it should look (and I can respond in kind, if it would help, although I don't currently have an 8" dome).