How long should I wait?

Unless she said something along the lines of, "I would love to see more of your work," then I would wait at least a month.

Thedrellum said:

Unless she said something along the lines of, "I would love to see more of your work," then I would wait at least a month.

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Yep. If you didn't get a personalized rejection, I wouldn't jump the gun here. There might be something in your writing style that isn't clicking for the agent (beyond the story itself not being a good fit), or the first query wasn't fully developed. This question is hard for me to pin without knowing what you sent.

I was querying two novels at one point, doing them separately. The ones that rejected the first one (and I was still interested in them seeing the other) I simply asked them, "Thank you so much for your response, would it be okay to query you with another?" I did this for quite a few of them and they all said sure, except one saying something about my writing style.

I don't think you should have to wait. Unless they say, don't query me again, I would go for it. Not every agent is polite in saying, "feel free to query me with future work."

And when I did do this, while they rejected one, some DID request the other, so it can just be they didn't like the story of the first rejection, not the writing itself.

All agents who accept queries will say yes, so long as the query they rejected from you didn't set off any alarm bells with them. Asking them if you could send them another query doesn't give you any new information: they're open to queries, so you can send one in. All it does is clog up their mailboxes, and give them more emails to work through.

I just wouldn't send both at the same time. Most of them say one at a time anyway.

I wouldn't send two at a time either. But after having one rejected, I wouldn't ask to see if it was ok to send the next. It's a waste of everyone's time. Do it or don't.

I've heard some agents say they don't like it when an author turns around and sends another query right away. Makes it seems like you have a trunk full of novels and when you get one rejection you say "oh, not that one? Well, what about this one. No? Well, how about this one?"

They seem to like seeing new queries from same authors (at least if they see promise in your writing) but with that quick of a turn around it just seems... off.

Generally, it's best to query just one novel at a time, so ideally you'd wait until MS #1 has had its time to shine before you hop to MS #2 (Unless MS #2 is really #1 and has already failed to acquire an agent, in which case you want to seriously look at the MS (and/or) query and consider either a revision or shelving it for a while). I'm sure there are circumstances in which it makes total sense to send a new query right after another, but I suggest being careful with it.

If you do send, I'd suggest mentioning why you're querying this MS (you said it seems like something she'd want.. mention that and why you think it) You might do this anyway, but at least you'd be casually explaining why you're sending another query quickly after a rejection.