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So I'm a research assistant for one of my professors this summer, and I pretty much have to ask him for a LOR. Is this a weird or delicate situation? Does it look bad that I waited to ask him till after he hired me? Also, finals are over so I'm not sure he's even going to be around campus anymore, but I feel weird about asking him over email. Thoughts? This post probably seems kind of lame but I am not very smart about this kind of etiquette.

If it matters, he hired me a couple weeks ago and I don't start until around June 7.

Ask him in person. This is too important to do by e-mail, particularly since you are asking him to do some work on your behalf "off the clock" so to speak.

It is a little strange since you will be working for him, but the fact that he can put that into his letter makes the awkwardness worth it.

The two professors I asked to write for me tried to talk me out of leaving, but it was balanced out by another Professor that I respected who essentially told me "If you get accepted, GTFO of here."

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I just posted a similar topic without seeing this one; my bad. I'm curious: did you see any issues with taking the position knowing that you might transfer? I'm trying to determine whether it's necessary to inform my prof of the possibility before accepting, in case he wants someone committed to the school.

I agree with asking in person if at all possible. Also, I would bring up the topic by asking about his/her career advice, and then segue into discussing transferring. It's probably also a good idea to frame your desire to transfer in as positive a way as possible (i.e., not just a prestige thing, but b/c of a specific goal such as geography, etc.) so that you don't alienate/offend.