Diamond is awesome and I love how you've started your dynasty. I'm hoping for lots of blueboos for Diamond and Thornton! Wishing you lots of good luck!
My Starr Dynasty was my first attempt and I had only been playing TS3 for a month when I started it - it went into the Hall of Fame in May - so it is definitely doable. I have a few words of advice for you.
1. Make back-up saves of your dynasty regularly. That way if a bug strikes you have a chance to go back to a previous save.
2. If your game is stable and doesn't tend to develop bugs very often - don't make any major changes (like adding an EP or to a lesser extent an SP). I purposely finished my dynasty before I installed Generations and it is a good thing, too, or I would not have been able to finish it for all the bugs.
3. If you have WA, travel at your own risk once you are allowed to per the dynasty rules. I traveled with no problem in my dynasty, but since Generations came out it seems like all the travel bugs are happening more frequently - at least for me they are.