Power up or save for 3rd blissey

Are you lacking other defenders?
not to sound like a broken record, but maybe wait for the "gym" rebalance before spending precious resources.

I'd wait if your gyms aren't too bad or only power up what you have instead of starting on another. 36 candies isn't a lot at the high levels and not enough to evolve and max one from level 20.

It takes a lot of candies to power up at the higher levels and trying to feed 3 Pokemon is very hard...unless it's common mons like Vaporeon where candies are sorta endless.

I have over 100 Chancey candies and only have 2 maxed.

I can take them both of mine to Level 38 now. I will evolve another when I get a good candidate and can max them all since I figure getting to Level 37 would take me a long time anyways and by then, assuming more catches/hatches, I can afford to max 3.

HB is way to easy to dodge to be a good defender against more than one attacker because if you attack with a buddy you cant time out against her.

To me, it's what you want from your Blissey. The higher cp and hit points it is, the tougher its going to be to get it out of the gym. Yeah, a 2200 will take a while and it is a decent pain lower down in the gym, but I made mine high (over 3000) to be up top and "sit there" collecting coins, and be a pain when someone does get to it.