Hi there! I'm a diamond dealer and jewelry manufacturer, and my family has been in the business for almost 100 years.
Honestly, there is a LOT to know about diamonds, and it's worth some time to get educated before spending $20k. This will take longer than a reddit post will allow, so feel free to PM me and we can talk off-line. For now, here are some quick answers:
1: No, there really isn't a "go-to" site. By definition, anyone selling online is a retailer, not a "wholesaler retailer."
2: As far as "value," there are two ways to look at this: resale value, and "bang for your buck." They are related, but not identical. For resale value, you will be primarily concerned with getting a "clean certificate." That is, something GIA certified, with no notes, comments, or issues what would complicate a sale. Something like a G color, VS2 clarity, with a really nice cut, will always be easy to sell. Then again, as far as "bang for your buck," I am usually an advocate of SI clarities (as long as they are clean to the naked eye) and high colors (ideally D-G). I tell people I work with "you need a loupe to see clarity, but you see color from across the room."
HOWEVER, in an oval cut, there is a more important consideration than either color or clarity, and that is CUT. Ovals are notoriously difficult to cut correctly, and most (90% or more) wind up with a significant "bow-tie" effect, producing dark spots in the middle of the stone. As an amateur, it will be very difficult for you to discern this until someone shows you, but you have to be really careful when you buy an oval. Putting a stone with a bad bow-tie next to one without this issue makes the difference really obvious.
3: That depends. Are we talking about a simple solitaire? That would be a few hundred bucks. Something with pave and some diamonds on the shank? Maybe $2k. Something with large side-stones, colored diamond accents, or more elaborate work? Sky's the limit. Once you know what design (roughly) you're going for, this will be easy to figure out.
4: No, I don't think that's too big. But that's largely a question of lifestyle. For reference, my wife is about the same size (5'4", 115 lbs - I hope she doesn't kill me for saying that!), and she wears a 2.75ct stone. It looks big, but not TOO big. Then again, we live in LA, and I do this for a living, so maybe my perspective is skewed.
Honestly, I think there's a lot more to know here. I'm happy to talk with you and educate you a bit, so you know what questions to ask moving forward, and how to evaluate the answers once you get them. Let me know if you're interested...