For basketball, yes, definitely. I'm actually in the process of changing them over on the dev site right now. Going to go with /basketball-hoops for the basketball pages. Just makes more sense.
As for swing sets, we have two main categories, outback and playhouse. Those two categories have a sub category that appends XL to the category name (such as outback-xl). Each category has combos 1 thru 5 and sometimes multiple or none of a combo (meaning you could have combo1, combo2, combo2-2, combo2-3, combo4 but no combo5).
I think the last time I did a count there were something like over 200 specific product combo pages. If we used AJAX it would reduce the actual pages to 12 (4 categories (including xl) and 3 heights per category). We have content issues with that site like you wouldn't believe and doing that would go a long way to fixing part of that problem but then it creates another even larger set of problems.
I think as a first step we will definitely eliminate /swing-sets from the paths of our product pages, though we'll need to keep the swing set overview page at /swing-sets. So once someone visits the overview page at swingsets.com/swing-sets, the sub pages would be at swingsets.com/category instead of swingsets.com/swing-sets/category.
Not sure there is really anything that we can do about the rest of the url though.
One thought I have after looking at your suggestion would be to go from swingsets.com/outback/5ft-playset/combo2 to swingsets.com/outback-5ft-playset/combo2
But again, I'm not sure if that makes any difference. I don't think anyone is searching for "outback" in terms of looking for a wooden swing set so I don't think we'd really benefit any by changing the / to a - in this case.
Actually, I just used the Adwords keyword tool to see and found that no one is searching for any iteration of {height} {playsets|play sets|swingsets|swing sets} so I don't think having that in the url helps any at all. Maybe having "playset" does but compared to all of the other SEO issues with that site I think it may not be worth worrying over.
So maybe swingsets.com/outback-5ft/combo2 would be just as useful. I think that's easier to remember. We do have landing pages for outback and playhouse but I'm not sure that should matter when making the path to the products. I think /outback-5ft looks better than /outback/5ft