The best thing would be if you learn to sharpen yourself. We can talk about the right way for you if you like. Some are inexpensive, some are easy, some work better than others. As you said, you can draw a knife through a machine sharpener as well as anyone else. For that matter, you can rub one on a couple of stones as well as anyone else but that will take some practice.
At this stage of the game, your knives may need to be thinned. Progressive sharpenings move the edge to a thicker part of the knife, and the bevel angles tend to become more obtuse. Thinning grinds away some thickness and allows you to restore the old bevel angles. File that under "good to know," for now.
There are other possibilities as well, but without handling the knife myself I can't diagnose the problem for sure. Bad sharpening -- even by pros -- could be a part of it. Considering how little sharpening you've had done, your knives are far from worn out. More than likely the problem is a combination of not enough sharpening and bad honing on your part.
You should use a rod hone frequently and with very little pressure. There's no right set schedule, you use it when needed. In the case of a Wusthof chef's knife that's going to be something like every other meal. If you're serious about getting the best performance from your Wusties, you may want to replace your hone. If you want to learn more about steeling,
read this.
Bamboo boards are very hard. Partly it's the hard, springy nature of the bamboo itself; but mostly it's all those glued seams. Hard glue is... well... hard. This tends to bend your blades slightly at the very edge making them seem dull. It's called burring, and is something to which Wusthof steel is very susceptible. The answer is to use your steel, and to change boards to a good hardwood board.
FWIW, bamboo is not wood, but grass. It's not good, but not the end of the world either. Bamboo is down the list from good hardwood and Sani-Tuff (which I don't recommend), and about equal to composition. It's better for your knives than any plastic I know of, and much better than glass or stone.
There are a variety of excellent boards from which to choose; but "excellent" and "inexpensive" seldom go together. We should talk about budget and size, before getting specific about boards. Regarding size, get the biggest board which will fit in your space and which you can afford.
Edge grain boards are better than long grain (aka side grain), better enough to be worth the substantial price difference, but not enough better to break the bank.
Just to ballpark you on prices, you might want to Google "Boos cutting boards." Boos is an excellent brand, and the prices are representative of the quality level. We have two boards, one an 18 x 3 Boos end-grain, maple, round "Chinese," the other an 18 x 24 x 2 Boardsmith, end grain, mahogany rectangle. While they're great for us, they may not be right for you.
That's a start on the subject. What are your thoughts so far?
BDL