For a "poor grad student" who wants a knife priced under $100, I'm sort of wondering why you listed 3 knives which cost more than $100 for a practical size (210 mm or 240 mm).
All that fancy Damascus cladding does zilch in terms of cutting performance. But it does make the knife much more expensive.
As for Alton Brown, can't say I'm all that impressed by any celebrity endorsement. Also, from my quick perusal of "Cut Brooklyn", $100 probably would not buy you anything there.
As for "Cut Co" - Yeeech! That's a brand (Cutco) which gets more rotten tomatoes figuratively thrown at its products than any other knife brand I have otherwise seen.
For $100, don't expect much. For a workaday real world situation, to have a good cutting system, you will need more than just a decent knife, you will need a way to minimize wear on the edge (meaning a decent cutting surface) and a way to sharpen the edge as it invariably gets dull in use. The last two are facts of life.
A plain 3-layer 210 mm Tojiro DP gyuto offered through the store you listed (Cutlery and More) is running $69.95 on sale. Amazon.com is offering the same knife at $50.10 today. Do the math, and see why shopping around pays off.
Look to see if you can find a decent end grain cutting board that won't damage your knife's edge. The cheapest I have found recently was through Ross ("Dress for Less"), which has been offering at various stores a "Catskill Craftsmen" 14 inch square by 1-1/2 inch thick with feet mystery wood end grain board for $17.99 (Model No. 91316). My guess is that the wood is Acacia and that the boards being offered are discontinues from Catskill Craftsmen. Before the bricks are thrown in my direction by the purists, I will acknowledge that the board is too, TOO small. But for just $17.99, it's hard to be too picky about size at that price range. To avoid having the board split apart (cheap boards can do that), don't pull the plastic off until you have bought some food-grade mineral oil and have it at hand. Safeway Grocery stores (at least around where I live) sell one pint for $3.49 in their drug and cosmetics area. Then, IMMEDIATELY after taking the plastic wrap off the board, start pouring oil onto the board, and keep putting oil on until the board stops sucking the oil up. Then turn the board over and do the bottom side as well. Do that twice the first day, once the second day, once the third day, once the fifth day and once the seventh day (and that's coating both sides each time until oil just won't go in). Now you're ready to start using the board.
Mind you, the boards were not being offered on-line. They were only physically found at the Ross stores. You have to make the effort to find the board, and not all Ross stores carried it. In fact, I was only finding one board at each store that did have one.
You still have about $28.42 left of that $100 budget (assuming you luck out on finding that board). For a system with absolutely awful stones (but better than nothing), look on eBay for a "fixed angle sharpening system" where the horizontal rod does not slide up and down a post. Take it from me, you don't want that "slide up and down" style. They have a fatal flaw. The horizontal rod cannot swing from side-to-side. Instead, look for a system where the horizontal rod perches on top of the vertical pole. And, as I also said, the stones are awful. Don't be surprised if yoiu need to replace the stones quickly.
These systems are a blatant Chinese take-off of an extremely good American-made sharpening system known as the "Edge Pro". But everything is relative and you will not be able to buy the Edge Pro for even your meager $100 (let alone a knife or a cutting board), so put up with the "Edge Faux" and watch Ben Dale's videos at Edge Pro's web site to see how the real thing works.
That's the best I can suggest for $100. It also doesn't take into account sales tax and it depends on luck on your part (to find the board) and the purchase and use of a rip-off of an excellent American product. But what else can be said?