I am in the same kind of position as you are PP. My LO will be 3 in a couple of weeks and still nurses at nap, bedtime, during the night and then the early morning too. I'm ready to gently wean but the key word is gentle and like you mentioned the LOs can cling harder if they aren't ready to give it up just yet. It's a line you have to walk with your LO and there aren't any cut and dry rules or magic that will speed it up though I'm sure you and I both wish that was the case! My LO is also still sleeping with us as well as not PL'd yet.
It seems to me that all these transitions that we ask our LOs to do are really big ones and doing any one of them too fast or too close together may backfire. For us I think that we will work on them all at the same time but at a slow pace. That way it feels more organic rather than pushed. I'd like to say that first we'll PL then we'll wean then move him into his own bed b/c that's how I'd like it to be but I know DS2 will balk at all the obvious changes so I know that working on them all just a little bit at a time eases the transition into the new world order.
I've also seen that when I stress about it he totally picks up on that and he clings harder. Then when I let go, he will surprise me and do the thing on his own.