can I ask HR to better explain their application instructions?

A reader writes:

I've been looking for a position for a few months and I've found the advice on your site invaluable in my efforts.

I am finding that often requirements for the submission of an application are written very vaguely and I want to make sure that I get them right. However, most of the online applications do not list an email address to which I can address inquiries. 

So my question is this: If I am able to find a contact address through some kind of search engine for corporate contact information (which is unverified).  Is it acceptable to send an email there with inquiries if no method of contact for HR is given on the company website or on the application itself?

I really don't recommend this, for a couple of reasons:

1. First, depending on the company, your email may not ever reach HR if you just send it to a general corporate email address. I'm not defending that -- I think companies should have well-trained employees who can recognize who a query is intended for and pass it along to the correct division promptly -- but competence is often lacking in the world, particularly when people don't feel something is their responsibility. And if it does reach HR, you may not ever get an answer anyway because HR is often swamped and doesn't have time to answer every question from candidates they don't even know they're interested in yet (again, not defending, just stating reality).

2. Far more importantly though, I question the idea of asking for clarification about the application instructions in the first place, because I think you risk looking like a pain in the ass. Look, I know some job ads appear to have been created by someone with zero command of the written language. But they're rarely impossible to figure out how to reply to, and if you're finding this "often," that tells me that you're over-thinking this. If you write to them asking for help understanding what they want (when they're getting flooded with applications from people to whom the instructions didn't give pause), some managers are going to sigh and think you're going to need hand-holding every time they give you an assignment. You want to show self-sufficiency and confidence here.

Now, maybe I'm wrong and you're truly running into loads of undecipherable instructions. If so, post an example or two in the comments section and we'll see if we can help. But I think this is a case where the best advice is to make an educated guess about what they're asking for and push forward.