MillionKnives is right.
What we talk about here is not about having $400 Japanese works of art. We're talking about what will work well. If it so happens to be $400 Japanese knive, then that's what's bought, used and maintained.
A goodly part of the issue is maintenance. If you don't keep the knife sharp, its usefulness goes downhill quickly.
The Chef's Choice 210 is an ultra-basic electric sharpener, with diamond surfaces for sharpening. What you get is an ultra-coarse edge, which will cut at first, but which will also leave an edge which gets dull quickly, so you need to sharpen sooner. That's going to wear the knife a lot more quickly.
Another few problems. Diamonds are relatively difficult to bond to any surface, so a usual process is to use a thick matrix to mostly mechanically hold them. Unfortunately, that mechanical bond is usually not enough to hold the diamonds for long, so the diamonds (beginning with the largest) are usually just knocked out of the matrix. Bottom line, over time, the sharpener loses its ability to sharpen.
Also, bamboo is really not very good for knife edges. Bamboo readily absorbs dissolved silica (the same element used in glass) from its water supply, and bamboo boards need to use a lot of glue (also very hard once cured) in their construction.
So, here's what I would recommend. Think of this as a three part issue. First part is knives; second part is cutting surface; and third part is sharpening system.
The first part means a good all-around chef's knife useful for the bulk of your purposes. Instead of a santoku, consider a different style of Japanese knife - the GYUTO. It is really the Japanese version of a French pattern chef's knife. It comes in lengths of 7 inches (180 mm), 8-1/4 inches (210 mm), 9-3/8 inches (240 mm), 10-5/8 inches (270 mm) and 11-7/8 inches (300 mm). If you want to stick with the shortest length, that's up to you. But if you carve any size of roast or similar large items, then the next longer length of 8-1/4 inch (210 mm) is probably the shortest practical length, with many chefs here using the 240 mm or 270 mm length instead.
I'm going to suggest a MAC BK-80 chef's knife. The list price is $110, but it can generally be found at discount on line for just about $90. It is by no means a "work of art", what with no "Damascus" blade and no metal bolster, but it's very good quality steel (much, MUCH better than anything you've used before) and will do everything and more than the santoku's you have been using, at just a little bit longer length.
With this knife, the handle is nothing you would want to really rave about. But, it works. And what you should also do is concentrate on getting used to a "pinch grip" as the way you hold the knife. It is what culinary schools teach their students to use - and your hands and (especially) your wrists will be better off in the long run with the pinch grip.
For the moment, if they are still working for you, then continue using your existing paring knife and bread knife. But when you feel the urge to replace them, then go to a restaurant equipment supply store and buy either Victorinox or Dexter plastic handled paring and serrated edge bread knives.
Now, the second part. A good cutting surface. This will be something that will be probably longer than the knives, if it is treated properly. And here's my recommendation for the least expensive really good cutting surface: a Michigan Maple Block 15" square by 2" thick end grain hard maple block. http://www.amazon.com/Maple-End-Grain-Chopping-Block/dp/B00O4CQIL0/ref=sr_1_4?ie=UTF8&qid=1440011941&sr=8-4&keywords=Michigan+Maple+Block
It's not absolutely ideal. 15 inches square can be more awkward than the usual 12" x 18" size. But for a really edge-friendly surface of end-grain northern maple, this is by far the least expensive board. Using it will slow down the dulling process significantly.
The board does need to be treated before first use. Get the least expensive food-grade mineral oil you can find (I buy my mineral oil from my local Safeway for $3.49 per pint - look in the pharmacy and cosmetic section of the store) and slather it on thickly multiple times on both sides of the board until the board simply won't absorb more oil.
You also need a scraper and a spritz bottle of full strength vinegar to clean the board. Scrape the board free of as much residue as possible, then a quick water rinse and light hand scrub with soapy water (NO SOAKING HERE), followed by a spray of the vinegar and allow the vinegar to evaporate. Your board will be clean and disinfected. Store the board upright and it will be fine.
The third part is sharpening. The least expensive method will be to use a stone. There are many good stones out there, but the least expensive version is getting a cheap Chinese stone (look in a Chinese grocery for them). The stone should be a minimum of 8 inches long by 2 inches wide, but almost all Chinese stones I have seen exceed those lengths and/or widths. Not very good quality, but they will work. Don't use oil - instead, soak the stone in water for about 30 minutes before using, and splash water on it for more lubrication.
Watch these videos of Jon Broida for techniques:https://www.youtube.com/user/JKnifeImports
And, you can read Chad Ward on sharpening here: http://forums.egullet.org/topic/26036-knife-maintenance-and-sharpening/
Hope that helps - and the spending here is held to under $150, not $400.