L.P.
I've never tried the diva cup, but I have use the Instead softcup. Similar idea. Different shape. It looks kind of like a diaphram - it has a flexible outer ring edge (that looks like a Livestrong bracelet, actually), and a cellophane looking cup attatched to the ring. Like the diva cup, it can be left in for up to 12 hours with no leaking, and no risk of toxic shock. Unlike the diva cup, it IS disposable, so not much more environmentally friendly, but more convenient, in that if you have to change it, you don't have to have a place to rinse it out before reinserting. You can simply insert a new one, if necessary. And another nice thing, is you CAN have it in during sex. No mess and you cannot tell it's in there. My fiance couldn't tell either.
I agree that you do have to be somewhat comfortable placing things in your vagina, and putting your fingers in to pull it out. I'd say that's the worst part, but truly NO big deal at all.
I definitely say either is worth a try. The instead is cheaper since it's disposable, and it can be bought at Target, Walgreens, etc. So that may be a place to start. If you find you like this kind of period protection, you may decide to try the diva cup.