First, I'm not seeing what types of foods you normally cook, so perhaps the best guesses by the rest of us is to assume this is for generic western-style "meat and potatoes" foods.
Since you are saying that the cutting board and the sharpening process will be separate budgets, I'll suggest the following (first for knives, then for cutting board, then for sharpening tools).
As for retailers, I've ordered from Chef Knives To Go, and I have not been disappointed. I have not ordered from Japanese Chefs Knife, though I have heard very good things about them. Japanese Knives Direct is the same people as Japanese Chefs Knife, but deals with non-culinary knives, so you would instead deal with Japanese Chefs Knife instead. Also good is Jon Broida at Japanese Knife Imports (as DenverVeggieNut noted above). As for Amazon, figure them to be "big box", much offered, good shipping, prices equal to almost anyone else, but zero knowledge or special service. That being the case, on occasion I have ordered from them. However, I limited my expectations to no-frills when it came to service.
First, the type of steel for the knife. You are admittedly someone with a minimal knowledge of knives. You are looking for a really good knife, but with minimal maintenance levels. That strongly suggest that the first knife be more, rather than less, stainless. While a carbon steel knife in the $250 range would offer a wonderful edge, it might be too much immediate effort to properly maintain (think RUST if you do not IMMEDIATELY deal with washing, rinsing and wiping IMMEDIATELY after use).
DenverVeggieNut's suggested knife from Jon Broida at Japanese Knife Imports is probably a good one, and while I have not seen or handled the knife in question, I would trust Jon Broida's selection for a good, workhorse stainless gyuto.
And in looking through various web sites for wa-handled gyuto's, not much appears, outside of the above.
However, I am also wondering if you should really invest much money in a first Japanese knife, especially if you have never used one before. I sort of wonder about your statement of "hating" western handled knives. If all you have handled is cheapo knives, with no sharpening, then switching to a Japanese-handled knife may be a bit much. Limiting your cost to $155 may be prudent here.
As for other knives, you're going to need a paring knife and a serrated edge bread knife. My advice is to not spend much money, but to get inexpensive, commercial-market knives. Look for a local restaurant supply house and especially for one which offers Victorinox knives. Or you can go online to eBay or Amazon.
For a paring knife, I would suggest following the advice of the former semi-resident knife expert, Boar De Laze ("BDL"), who suggested getting cheap, fibrox-handled Victorinox paring knives. They run in the $5-$7 range per knife. My recommended blade length and shape are 3-1/4" straight-edged spear point or sheep's foot. Stay away from serrated edges on the paring knives. And you don't need a bird's beak. Here's one from Amazon:
For a bread knife, BDL waxed poetically about the 10-1/2 inch MAC Superior bread knife. But with a price now approaching $100, I would instead suggest a 10 or 12 inch Victorinox serrated edge bread knife.
For a cutting board, end grain is simply the best way to go. Certainly, DenverVeggieNut is right about the quality and reputation of The BoardSmith's products (though I simply cannot afford them myself).
However, on a budget, I would go for a stock, standard board, The big names are John Boos and Michigan Maple Block. I would suggest the following:
The retailer is an authorized on-line Michigan Maple Block retailer, and the price (with free shipping in the USA) at under $50 is better than anything else I have seen for at least a year for this board. (It's good enough so I have just ordered another for myself today) I do suspect that this is either a limited time offer or a limited quantity offer. Michigan Maple Block has in the past sold through Overstock.com, but that offer ended a year ago and I suspect that MMB might be spreading their bargain excess capacity value boards through selected and favored local e-tailers.
Upon getting the board, you should immediately saturate it with food-grade mineral oil. Put it in or above your sink (to contain the inevitable spill and just lather on as much mineral oil as the board will take, both sides - then wait and do it again (and again and again), until the board simply won't accept any more oil. To save money, I would also suggest the cheapest possible food-grade mineral oil. I shopped around and found the cheapest for me was $3.49 per pint at my local Safeway. But if you can find it cheaper, better for you and your wallet.
Now about sharpening - until you start sharpening, your knife will start to get dull and will remain that way and get worse until it is sharpened. That's just the nature of edges. Learn to sharpen, and you will more than compensate for all those past el-cheapo knives. Ignore sharpening, and you should just continue to buy cheap knives. It's that simple.
Plenty has been written on sharpening, including this on eGullet:
It's the condensed version of Chad Ward's Book, An Edge In The Kitchen, published in 2006, and with the book likely available in libraries or through inter-library loan. The prices in the book are hopelessly out of date, but the info is still good.
Also, on-line videos from Jon Broida and CKTG are very instructive.
The first tool you will IMMEDIATELY need will be a ceramic honing rod. Avoid steel "sharpening steels" and just get a ceramic hone. Length does matter, so my quick recommendation is the 12 inch Idahone (Chef Knives To Go, $30).
A combo stone is a quick and inexpensive way to start sharpening. DenverVeggieNut's King Combo stone is pretty common.
As for me - I am a EdgePro Apex user at heart.
But whatever you do for sharpening, the key is to try.
Hope that helps