Macau and Hong Kong are really easy for an English-only speaker. I didn't bother with the Chinese Visa (I only had four days) so I don't know about the Chinese side, although I don't imagine it will exactly be very amiable for Westerners outside of Shenzhen. You've gotta remember that many of these places were backwater villages a few decades ago and now are cities with millions of people, so they can be a bit bland.
Macau is a very interesting place, however. The central (government) area feels a lot like the center of a European city; here's a pic from when I went:
Slightly uphill to the north is the facade of the St Paul Cathedral, and the Macau Museum.
But looking across the river to Nanping (on mainland China) and even towards the border area of Macau was a bit less uplifting:
But I wouldn't say the southern areas of Macau are dreary at all. Macau's streets are windy and fun to walk down, and you come across interesting things very often just by wandering around.
Of course you can gamble, but I didn't like the casinos anywhere near as much as Vegas casinos (I went pre-Wynn). There was no poker and you have to pay for drinks. And all anyone plays is Baccarat. And they focus absurdly hard on it.
Hong Kong is easy and pleasant. Check out the Po Lin Monastery on Lantau for a bit of Buddhist flavor, and pretty good hiking (if you like that). Otherwise the city itself was my favorite thing. Walking the boardwalk on the Kowloon side of the bay is imperative--it gives a truly fantastic view of perhaps the world's best skyline.
It's good that you're going during the winter. I went during the summer and the monsoons made the whole trip a bit less enjoyable.
Have fun