There's a range of prices in what you're looking at, and it's very hard to say whether spending more is "worth it" or not -- it'd be hard to say for myself, and next to impossible with someone else.
My own take on some of what you wrote -- and this is just a point of view, and some prejudices, not anything like Truth -- is that the Tojiro used to be a supremely high value, because they used to be much less expensive than they are now. I don't know the macroeconomics of the situation, but my guess is they were VERY popular and recommended based on price and just the difference between what Euro-knife users were used to. But they got popular enough to raise prices and keep a lot of good-will. They're still well-priced knives, I'm not contradicting that. But they used to be such an easy first choice for someone who has not used something similar because it was a very inexpensive entree into this new world.
The Tojiro is a "clad" knife, too (or "san-mai" or "warikomi"). Which means the middle layer is a harder steel with softer steel wrapped around it. They sell this as if it's a big advantage. Some people don't care at all, some care a lot (think it mutes the feedback of the knife against the board, or against food). This is a minority concern, evidently, but it's one difference between the Tojiros and the Mac or the Masamoto. Tojiro also has a blockier handle which is not as good, but might not matter to you. (Truth be told, I like a nice handle, but I like how my perception of "nice" looks about as much as I care about how it feels. That is, unless it's one of those hump-backed "ergo" handles, I seem to get along with most any of them just fine. Fewer or softer "corners" is nice.... but I'll stop talking here, because I think it matters less to me than I thought it would, ever, prior to trying a variety -- and it may matter a lot more to you).
All that said, I have a Tojiro parer, which sees the occasional apple peel and otherwise a lot of darkness inside the knife block. I haven't used a clad cook's knife to know if I dislike them for reasons described as the minority-view problem above. And now that I've already typed too much for someone who has only read about some of these issues... I'll recommend searching the history of posts for "Tojiro" and reading about them from someone who has used these types of knives, both on the cladding and the handles.
The Mac -- great knife, no real downsides, but higher in your price range. There are lots of posts (if you just do a search) comparing the Mac Pro to the Masamoto VG, and I won't rehearse them here because I haven't used the Masamoto. Never held one, even, much to my chagrin. But you're talking knives on very close to the same level, or the same level, here, just with slightly different strengths.
All that said, I think if price doesn't make the call for you, don't bother with the dimples. Really they're ignorable... eventually they might get in the way if you're sharpening and thinning behind the blade for years to come (which is probably not an issue), so the downside is almost fake; the upside is that food doesn't stick to the knife when you're cutting -- and that's probably not true, or not noticeable, or not in almost any circumstances. So the upside is also almost fake. Don't worry about it.
If you want to develop a good grip and some basic skills, then a longer knife will make you happier in the long run. I think with knives this light, there's not any particular comfort even for a beginner in a 210mm knife. If you plan on using a hammer-grip and don't really care to improve, then maybe whatever you're already used to will be more comfortable for you. (And actually while on the one hand this is a bad idea, on the other it's still fine -- and better to have a sharper knife than what you're used to, so you still get to play the "which knife?" game!)
Depending on which knife you buy and how the bevels are ground... yes you want something like the Ceramic rod hone. Clearly you're looking at the Mac. You can spend less on the Idahone fine ceramic honing rod (from chefknivestogo.com or from Dave Martell's site). It will break if you drop it. And get the 12" if you end up with a knife that's 9" or longer. I haven't used the Mac one -- I believe it's sturdier (steel core?) and not quite as fine, but that's hearsay that might be misremembered (as hearsay always is) anyway.
The rollsharp -- some people are happy with them forever. Another thing there are many posts on here about. And again you're getting this from the Mac site, no doubt. It will give you a much rougher edge than can be done by hand sharpening. And a less sharp edge, too. But it's do-able by someone who doesn't want to be bothered with either the expense of better options or the time involved in learning to make use of better options, so that's your call. Here I think (and maybe I'm in the minority), if we're talking about the Mac, it's STILL so much better than most European knives, thinner than any forged knife, that it might sever really well. On the one hand. On the other hand, the knife has enough more potential than that, which is why you're paying a relatively high price for a knife, and if you're not going to bring it to that potential, maybe it's not worth it. (?). Maybe have a look at the Forschner's (Victorinox) Fibrox knives. (Or the same knives with the rosewood handle). OK I just re-read what you wrote... no I wouldn't recommend using this between sharpenings... if you are confident you can do a decent job sharpening, then skip the rollsharp. It's not an in-between-sharpening maintenance tool like a honing rod is. It is a sharpener.
CarboNext -- good knife, thin blade, but you'll be committed to sharpening on stones. It won't come to you with a good edge (the Mac would). That and... what's good about it is it WILL take a good edge if you know how to sharpen.
Gekko -- I really don't know at all. It's not my idea of "pretty" which seems to be one of the sellling points. (I DO like some Damascus or Damasc-oid knives, to look at, but that's not one of them. And there aren't many of them, actually. So I haven't really explored Gekko at all).
I like the handle on my CarboNext, the knife is pretty, the knife is very easy to sharpen, it keeps a good edge. My "F&F issue" is something I didn't notice until I sharpened, and that is it has a slight overgrind. In other words, on the face of the knife, if held against the light and looked at down from the handle to the tip, there's a small area that looks dished where it should be perfectly flat. This will only be an issue if that dishing is deep enough (it may not be) that when the knife is thinned to the point closest to the blade, it makes the bevel "dip" too. Not an issue so far, and it might never be But it might. And I don't have any idea if this is something to be concerned about for other people, or if mine is anomalous. But you won't run into this with a Mac, I'm sure; and again, the Mac will at least come sharp out of the box, so you'll have some time on it to see what it's like before having to deal with sharpening. (A good sharpener will get it sharper than OOTB, right away even, too though).
So laying my prejudices on the table -- I'd go for the Mac Pro or the Masamoto VG. Or down a price point, you wouldn't go far wrong with CarboNext if you are ok with sharpening.
I got distracted above by the rollsharp question, and "missed' that you're planning to sharpen (presumably on stones). Sorry. I won't re-write though, because I think I foregrounded some of the questions you asked even by missing this. And I'm a fast typist, but a lazy thinker.
