Olivia,
Thanks for your detailed post.
From what it looks like, you do try to keep your lo in a good routine. You say that your DS is spirited, hence it is really important to get him onto a good routine, this will make both you and DS a lot happier.
I definitely suggest setting a few days out to try and get your lo onto a good routine. Start as you mean to carry on, once you are on a good routine, everything will settle into place
Lets say for instance you start your day at 7:00 am - you are going to have your E A, wind down, and get your ds ready for his nap. Start your wind down routine a few minutes before you see the first sign of tiredness, so that your lo is not over tired by the time you get him to bed.
Ensure that he is in a very darkened room, Do you swaddle? give, pacci, put him to bed awake. You say that your lo usually wakes up at the 45 minute mark - this is usually the case, where they jolt before transitioning into a deeper sleep. You could go in there before the 45 minute mark, pop his pacci back into his mouth, and keep your hand on his tummy, to help him get through the jolt and go into a deeper sleep. He may wake slightly, but you can pat / shhh to get him back to sleep. This usually helps with extending his naps. You may have to do this a few days to help him transition.
Some lo's do have a routine that looks like E A S A E etc. it is not uncommon, but you do want to work on extending your DS's naps, to ensure he does not get over tired / stimmulated.
The cluster feed will definitely help your lo go longer, and also may help him not wake up for his dreamfeed. Let me know how you get on with that.
With regards to your question on what you do when you are out and about - you are always going to have days like that. The best thing to suggest there is, if you go out and about, and your lo is completely off routine one day, it is recommended that you try to say indoors the next day to get him back onto routine.
HTH, let us know how you get on.
Paula x