Dropping the "Dr": When to let formalities go?

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I am a PhD student towards the end of my program. As I am interested in research more than teaching, naturally, I am searching for post-doctoral research fellowships. As such, I have been contacting several tenured faculty members recently and engaging in conversations about research, funding, timing, etc. In any case. I find myself delaying sending a lot of these emails because I'm not sure the appropriate level of formality to keep between me and these faculty under whom I would like to work. Many of them respond to emails with just their first name, or a nickname, though all of them are PhDs, and many are acquaintances of mine. Normally I lead with a very formal email, but how do you know when it is ok to drop the "Dr." ?

In general, two PhDs when talking to one another just call each other by first names, but I'm not quite a PhD yet.
A lot of PhDs ask even college students to call them by their first name. In general most people will tell you what they prefer to be called, but what do you do when they don't tell you?

I think it's a little awkward to respond to an email from a faculty member that has a smiley face in it with "Dr. Smith, ..." but maybe it's just me.

Are their any other PhDs or PhD students out there? What do you do?

On first contact, formal is always appropriate, as you say correctly. After that, I think the general principle is to follow the person's lead in how they sign themselves. If they sign themselves "Dave," then it's normally acceptable to address them as "Dave" in a follow-up. If they sign themselves "David J. Daystrom," then I'd continue with "Dr. Daystrom."

It's never wrong, though, for a junior person to continue in the formal mode, even if the other person appears to write informally. This is especially true while you're still in the midst of applying for a job or student position. After you've got the job, informality can prevail.

(Dr.) Darmok

I agree with Darmok. Whenever I apply for a position, I use the formal approach (Dear Dr. XXXXXXX,). It is the safest way to go in my opinion. If the other person responds that they would rather be called by their first name, the formality can be dropped at that point in time. Otherwise, it is best to stay in formal mode.

I drop the Dr or Prof on the first reply from them.
All PhD I know sign their email with their first name or nickname.

When in doubt, keep the "Dr".
A decent rule of thumb is to match your replies.
If they sign their emails without "DR. XXX", it is safe for you to leave it out of the lead next time; if they sign with their first name, you can open with their first name next time.

basically, open the same way as they close, and always use the most formal form in a first contact; it never hurts to be too formal.

As a general rule you drop formalities when the other party tells you to. It is probably different among faculties and cultures, but in my experience as a medical student working with MDs they usually tell me to call them by their first names in the first meeting, but I never assume. They earned their title, it's their decision whether they want people to use it. And I have known a few people who are really uppity about it.