Let me see if I have this right:
- You want to buy a great knife;
- You don't know how to sharpen, but want to learn;
- You don't want to learn to sharpen on the great knife; and
- Your total budget for knife and sharpening gear is $300.
First, buy a 10" Old Hickory butcher's knife. They're less than $20, very useful as heavy duty knives, will teach you everything you ever wanted to know about caring for carbon, will teach you everything you never wanted to know about caring for carbon, and will provide hours and hours of sharpening fun. Get it sharp, learn to care for it, sand the handles down, crown the spine... and you've got a helluva chicken splitter.
With that out of the way, the next step is buying a sharpening kit.
You can get a decent combination sharpening stone for well under $100. Add some way (any way) to flatten, and a decent honing rod, and you're looking at a bit over $100. You can get a good pair of stones (you'll need to add a third stone down the line), plus an inexpensive diamond flattening plate, plus a decent honing rod (aka steel) for around $150. IMO, separates are worth the money.
A decent, entry-level yo handled knife can be had for under $100. The usual suspects are the Fujiwara FKM, Richmond Artifex, and Tojiro DP. They're all fine.
The Fujiwara is a nice knife. A little low at the heel. Nice profile. Mediocre alloy.
The Artifex is made from an extremely good alloy, has great edge characteristics, but its cosmetics are mediocre. Of the three entry-level yo, it's my favorite.
The Tojiro DP is constructed from similar materials as the Shun Classic but doesn't have the tarted up faux Damascus pattern and doesn't have the clunky German profile either. At half the price, it's twice the knife.
The next step up the ladder of yo-gyuto pricing is the Suisun (western) Inox series. They're extremely well finished, but made from the same mediocre AUS-8 alloy as the Fujiwara FKMs. Whether the better F&F is worth the money or not, is up to you.
While there are a few yo-knives worth discussing -- if you or someone else brings them up -- in the $135 - $175 range, the real action in high quality yo-gyuto is at the near $200 level. I particularly recommend the MAC Pro and Masamoto VG.
Richmond has an entry-level wa-gyuto on the market. It's manufactured for them by Fujiwara, made out of AUS-8, and is supposedly very much like an FKM in respects other than weight and handle. I've never tried it. If you're seriously interested in a relatively inexpensive wa-gyuto, it's worth a shot.
After that, the Gesshin Uraku is a big step up -- around $150.
At just under $200 there are a few Richmonds -- Addict, Laser, and Ultimatum -- worthy of interest. The Sakai Takayuki Wa-Gyuto is very nice as well.
I bought a Richmond Ultimatum a few months ago which -- after some getting get used to -- I love. Cosmetics aside, it's very much the wa equivalent of a carbon Sab in terms of versatility, robustness, and feel on the board. Mine happens to be carbon (51200), but they're available in a very good stainless (19C27); as well as the ultra-deluxe, ultra-trendy, fantastic edge-holding, powdered metallurgical stainless, Bohler 390.
Ball is in your court. Start talking about what you want with some specificity, and ask a LOT of questions.