QTPie, just found this thread. Can I ask, how did the "retentive" thing sort itself out? My daughter is holding on for very long periods of time and looking very uncomfortable while she does. She sits on the potty lots during the time she's looking so uncomfortable but still can't seem to wee. Yesterday she didn't wee from 8am until 4.45pm, drinking lots and lots during that time. Did you find anything that helped your son wee, or does this sort of thing just get better with time?
DS was 2 years 9 months when I potty trained. I did a week indoors to begin with, then after that "out as normal" in pants (no nappies, no pull ups).
DS was "retentive" when I trained rather than a "pee anywhere" kind of child - so I was actually fairly confident that he was not likely to start peeing everywhere. I carried a bag everywhere with changes of clothes, wipes, and pull ups incase I lost the will to live (I didn't and they went unused). Started training at end of October, only one accident out since (that first week of going out, after swimming, in a cafe - probably not surprising since he drank half the pool).
All are different: just working out what is right for your child and what grief you are prepared to put up with and going out prepared.
I was just about to post about this. My DS is also 2.7 & we introduced the potty casually a few months ago but this week we have been in all week while he gets used to using it & going regularly etc. but as you said OP, it's taking DS out in to town that's going to be tough. I'm planning on doing short journeys to my mums & home to see how he does first before braving the town. Will be watching with interest. Good luck with potty training your DS