It certainly happens, (I think it happens more often than is talked about online) and when you do the math D&D can be a fairly cheap hobby if the costs are shared.
One thing I see infrequently is asking the entire group you're playing with the share in all of the costs. Also, I've found that some of the player maps on DDB are not great - for example the PC version of Icespire Hold from DoIP shows all of the secret passages but those maps are typically fixed for Roll20, because things like secret doors are added as images on the GM layer. I've purchased all my sourcebooks and adventures on DDB, and then repurchased the adventure modules on Roll20 as needed, which is expensive, but for me it's worth it to not have to set up the maps and tokens and dynamic lighting.
I'm doing the same thing - I much prefer DDB for content and character sheets, and so I use that for my players with the Beyond20 extension for making rolls on Roll20.
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