I would add, that if you are considering going digital, then you should consider all the digital options and not just DDB. T me, DDB is kind of the half-way house, and is more like an introduction to what you can do with D&D digitally. It works great for many people. But for me, I went digital and I decided I wasn't going to invest in something that only went half they way towards what was possible.
Consider going to a full VTT that has D&D content. There are pro and cons to each one. To me, one of the big consideration is if you end up owning or just borrowing what you spend money on. If you want to go full digital, and want what you buy to not be able to be taken away from you, then Fantasy Grounds is your choice Just be aware, just lie everything, it has its cons too.