I'm probably going to be jumping around in trying to answer your questions, so try to bear with me.
I feel your pain here concerning avoiding fees. And the best suggestion here I can think of is to strictly prioritize your spending. Getting a new knife may be a bit of excitement (it's something you can hold in hand), but getting your existing knives sharp, keeping them sharp with a good ceramic sharpening rod, and a subsequent sharpening system, and using a good cutting board may have a much higher immediate cost benefit aspect, which will also be usable decades down the road.
And I will harp again on going to your local library and reading Chad Ward's An Edge In The Kitchen. If your library doesn't have it, it's probably available through an inter-library loan network. And borrowing it through the library won't cost you any money - just effort.
At least for myself, I am comfortable about ordering from afar, sight mostly by picture, text and separate research. The reason is because of a sad truth - really top level products in kitchen cutlery are not normally found anywhere except in small isolated (from one another) shops, which are few and really, really far away from one another or from the general populace. About the only way you can get some of the best products is to go the internet route.
There is really a dual world here. Top sellers, such as Wusthof and Henckels, got that way because they developed sales networks and contacts when other knife manufacturers failed to push sales representation in the United States. Their success today is as much about the fact that they are the last widespread sales knife makers, except for the really inexpensive Chinese-factory knife manufacturers. When Macy's became the last truly national brand department store, what Macy's is offering becomes the "quality leader" that chains like BB&B will follow. It's not likely that Macy's will bad-mouth their top-of-the-line offerings.
Another issue here is production consistency and mass production quantity. Macys and chains like BB&B need consistent quality in their products - and production facilities capable of churning out knives in volume. By example, Wusthof uses X50CrMoV15 steel in their best knives - chosen as a compromise, as much because it can be heat-treated to avoid chipping (having chunks break out of the edge of the knife) as to provide a cutting edge. Having a knife you can use in whacking a boned roast without having the knife edge flinging off chunks of steel is valuable to many chefs - they don't want to have to run to the cutlery shop mid-production during dinner hours.
On the other hand, Japanese knives are more like high-end craft makers, rather than mass market manufacturers. They don't make many, but their quality is much higher on a piece-by-piece comparison. Top Japanese knives use different steels specifically designed for cutlery, and heat treated to harden the steel as much as the makers dare risk. The result are knives which will take a sharper edge and hold it longer, but with a greater risk that the edge can fail or chip, if abused.
Le Cordon Bleu is really a long-ago-discontinued line from Wusthof. What you are seeing on Amazon is the remnant stock being sold through the Amazon webstore by another, much smaller retailer. It was subsequently replaced by Wusthof with the "Classic Icon" line - the primary difference (as far as I can tell) being the replacement of the traditional handle of the LCB (and the "Classic" line) with an "ergonomic" handle on the "Classic Icon". Removal of the full bolster is certainly an improvement over the "Classic". Wusthof also changed their heat treatment process a few years ago, to increase the hardness of their knives to 58 Rockwell Hardness testing. Whether the LCB has the older, softer steel heat treatment or the newer harder steel heat treatment is something I don't know.
In your original post, you mentioned Miyabi Evolution. Since that is a line supposedly exclusive to Sur la Table, I am presuming that you visited a Sur la Table store to handle the knives. I would suggest that you go online to their website and browse through all of their on-line catalog to see what might else be available that you can touch. (The other big box upper-scale home retailers are Williams Sonoma and Crate and Barrel).
1. Sharpening. Because a single bad sharpening session can really do a horrible job on a good knife, I would first do a lot of checking around on what any particular professional sharpener is able to provide in services, as well as the quality of services. You might also try out the sharpener by taking one of your older, more expendable knives to be sharpened. Then carefully look at the evenness of the bevel of the edge, including looking at both sides of the blade.
In my own experience with an outside "expert sharpener", at a family-owned vacation house, where I don't really have much influence, one sister-in-law took the kitchen knives to be sharpened to a "professional" sharpener. The result was a nightmare. It seems the "expert sharpener" was mostly expert in getting the word "expert" spelled right (unless that was spell-check). So, I'm quite skeptical about taking knives to a service.
However, that will be your choice. If you do go the professional sharpener route, first ask about getting the bolster reduced. If the answer is "No" or "It isn't needed" or some other put-you-off answer, then take your knives elsewhere. That person is flat-out not an expert. And you will need to get the bolster reduced before your first sharpening, if you are going to treat the knife right.
You should also get a honing rod (what is often called a "sharpening steel"). It's not really for sharpening, but for microscopic edge alignment, and will vastly prolong the amount of time between sharpenings (it's the sharpening process which creates the wear on the knife. The more times the knife is sharpened, the faster the knife is worn). For your honing rod/"sharpening steel", get a smooth ceramic rod - one of the best is the Idahone (about $30).
2. Your type of cutting sounds like you will be doing almost every type of cutting experience. Tomatoes will be thick-skinned, with a soft interior (so you might very well justify a separate serrated edge bread knife). Butternut squash will be a good test of sharpness, which would work well for a good Japanese gyuto. And going through any boned meat may very well justify one of the non-japanese knives, such as a Wustie.
3. I would give a high priority on replacing your cutting board. Neither acrylic nor polypropylene are particularly edge friendly, especially to Japanese knife edges. Polypropylene also runs the risk of developing and retaining cuts, cracks and grooves, which can (and are likely to) retain microscopic food remnants, which will end up as grist for pathogen growth and passage to your foods later. Health inspectors often cite restaurants precisely for that reason.
Best choice, but most expensive, is a properly built end-grain wood cutting board. Hard maple is the usual standard against which other woods are compared, but other woods can also be used, as long as they are closed grain, rather than open-grained (such as oak). Be sure to check a potential end grain board carefully before purchase for cracks and gaps. Then treat it several times with lots of mineral oil before first use (a new board will soak up a lot of mineral oil). See the forum for suggestions and critiques about various makers, both stock and custom. And then scrupulously follow cleaning procedures after each use.
In descending order of preference after end grain boards, an edge grain wood cutting board (also treated with mineral oil) is next in preference. Then comes composite boards and bamboo boards, followed by plastic boards. Anything harder, such as glass or ceramic or (shudder) marble or granite, should be considered as strictly decorative, and should never be used by a good knife.