Is there a way to get around what seems to be some very ridiculous online application processes? Redundant questions (like what grade school you attended, and major declared!) make me want to put a shoe through my computer screen. I'm applying for positions that demand skilled labor and have whipped up some pretty attention-getting letter and resume material (both verbally and visually). Having to turn this effort into plain text pasted into type fields ruins my layout efforts, breaks my heart, and not to mention, decimates all the work I did to try and stand out from the crowd.
But I never say die. I've dug around and have usually found the business email address of the company's HR screener or even the likely person I'd be reporting to — and even from the companies that are working really hard to stay anonymous. I then send my stuff as an attachment in an email. I have a pretty good subject heading, and figured if I got this in my box I'd open it even out of curiosity. My rationale is that I'm hoping the strong content of my letter and resume will grab the person's attention enough to want to just contact me themselves (or pass it on to HR) since this is who I'd likely be reporting to anyhow.
Is this kind of boldness (and what I like to think of as ambitiousness) in reality ruining any chance of getting contacted?
In some cases, probably. In other cases, maybe not. Different companies work differently. At some places, if you don't use the online application system (which they required you to use for a reason, such as that they can't get you into their applicant tracking system otherwise), you're not going to get considered. At other places, that may not matter so much.
But does this come across as particularly bold or ambitious? Candidly, not really; aggressive, yes, but that's different from bold or ambitious. And you risk coming across as an "instructions don't apply to me" type.
I'm further worried by your mention of "attention-getting" visuals and a curiosity-inducing subject-line. Sometimes these things can work, but when they don't, they can be really bad. And the owners of the bad ones traditionally are poor judges of whether or not theirs fall in that category.
I get that you're trying to stand out in a crowded field. But the better way to do that is by being a really strong candidate, and I get the sense that you might be putting more of an emphasis on gimmicks.
(And think about the type of manager who you're self-selecting for by using this approach -- one who responds to gimmicks over merit.)
If you really want to grab attention, find a connection to this job or company and have them personally recommend you to the person doing the hiring. That's going to serve you a lot better than a notable subject line or a visually stunning resume.