I can't give advice on bottle breaking, as my little one gave up the bottle and insisted on only the breast from 12 months on! However, my advice would also be to NOT try to do both at the same time because that is too much change at once. I also think tackling the bottle first makes sense because it will go quickly whereas potty training will take a little more time.
My daughter just turned two and I am actively potty training her now. She is doing fantastic and has been regularly using the potty since the 2nd day with only very occassional accidents (we are 2 weeks in). I read a great book called "The no-cry potty training solutions" by Elizabeth Pantley which has lots of great ideas.
More specifically, I attribute my daughter's relatively quick success to several things. First, before actively starting, we got several children's books about using the potty. Look for ones that are fun, but that actually describe and show very clearly each step. Or make one yourself using picture you take of you or he playing, stopping play, walking to bathroom, pulling down pants, sitting on potty, wiping, washing hands. Me and my daughter's favorite is "Big girls use the Potty" by DK publishing. I'm sure they probably do one for boys too. Then I talked up going out and picking out a potty for her for a couple of days. We went, made it super fun, let her pick the color, etc. Got it home PUT IT IN THE BATHROOM, let her sit on it, put her dolls on it, get comfortable with it, etc. for a couple weeks and talked about how soon we would start going pee/poo there instead of in the diaper. Then I bought/made 30 little "prizes" and wrapped them up in wrapping paper and bows and all and put them on the mantle- out of reach, but in sight. They were just little things like a sheet of stickers, jar of bubbles, a book, a bouncy ball, a mini-tuperware with some florist marbles in it (one of her favorites-- she's played with those for hours and hours), wooden animal figurine, big girl underwear, etc.
Then I turned up the heat and when we were around home, let her go naked from the waist down for 2 days and told her to tell me if she needed to go pee/poo and we would go to the potty. Told her that when she was ready to start using the potty, she would get a prize each time she did. Kept it all really fun and low pressure. She had a few accidents and almostly immediately became in tune with the feeling of needing to go and started telling me. After that first two day intro was over, we switched to big girl undewear (a strategically timed prize) and pants around the house, but still a diaper on when we went out, for naps, and at night. When the prizes ran out we made a potty success chart together with glitter glue and all that now she puts a sticker on each time she goes that day. She is so into it and so proud each time she goes and washes hands. Just two weeks after starting, we are now leaving the house in big girl underwear and using the big toilets when out and about with total success, but always trying before we go anywhere or get back into the car to return home. Her night and nap diapers may stay a while though, to be sure she is biologically able to hold it that long. It has all been a bit time and labor intensive (it can sometimes be hard to muster lots of excitement for her about that 9th pee and 8 pm...) but considering I'm not spending any time changing diapers or washing them (we used cloth) and soon all this hubbub around going will subside, it is most certainly a good trade off!
Sorry so long, I got carried away. I'm just so thrilled with her quick progress and hope what has worked here might help others out there tackling what seems a rather daunting undertaking. It doesn't have to be! From my recent experience, it seems it can be fun and a great self estem/independence builder for your little one at the same time! Good luck!