stealthbanana, I would say your first problem is as a direct result of your second problem. And that they are effectively one and the same thing.
This wanting to stand up thing is a nightmare phase, it needs you to be consistent and insist on baby lying down and being relatively still in order to go to sleep. On this basis, you holding him isn't great for the long term, it would be much better done in the cot.
As you are going through a phase of it being difficult to get him to go to sleep, it's going to be therefore difficult for you to know when he needs his naps. Because him refusing to go to sleep 2/2.5h after waking in the morning might be about inconsistent settling method, not that he's not needing the nap.
To answer this: But HOW do I get him to take a first nap between eg 9-10? in relation to my paragraph above, I would basically just insist that this is nap time and is not negotiable. To do that it needs you to sort out an "I mean business, you ARE going to sleep" settling method.
You mention holding him to your chest to still and calm him to sleep. I would take that idea and move it into the cot. So involves lots of leaning into the cot. Hands on chest/legs in a gentle but firm, cuddle kind of way. Any struggling against you and loosen the firmness, lift very slightly (a few cm) and put back down, starting the resettle again. Repeat a million times...
As for the timing of the routine, I would recommend setting an 11am limit to your morning nap so that second nap is 2pm. The aim then being 9/9.30am-11am and then 2-4pm, with a 7/8pm bedtime and expecting a 7am ish morning.
I've never bedn a fan of the Gina Ford short morning nap. All four of my children have kept a long morning nap and a long afternoon nap, until the morning nap moves later and merges with the second nap to make a gigantic 3-4h single lunchtime nap.
No idea whos routine that is (in terms of published authors). But it has worked best with all of my 4 very different sleepers.