Here's my 2 cents...
Wait until after the road trip for the training. I always accept that on vacations my kids will not sleep as well, and I will have to get them back to their good habits when we return. So doing new sleep training while away from home is just too hard, I think!
Next, I think you need to do the whole sleep training at the same time - naps and bedtime. Otherwise, it's just too confusing. I know it's hard, especially at night, but I think if you stick with it you will be happy with the results!
Finally, do it now! As your baby gets older, it will get harder and harder to retrain bad habits. I know it's so wonderful and easy to nurse them to sleep, but it's even more wonderful and amazing when they go down on their own!
Good luck.