I know what you mean and also struggle with this, I’ve used and own both Trail and Race Shimano pedals.
I don’t find the Trail easier to get into but they do offer a platform that I can push against if I’m not able to clip in and get up the hill.
What I’ve found makes a difference is the shoes, my carbon bottom slippy Sidi can be awkward and it’s a bit dancing on ice, where as a treaded SPD sole helps with purchase.
I also find it easier if I’m not in my easiest geR, so I’ve got some resistance when I turn the pedal.
I’m thinking of going back to trail type shoes over my XC racing snakes.
Exactly this. Different shoes for different Pedals. Sidi XC Shoes are a slippery bugger for XC SPD (but are super stiff sole), Whereas Shimano XC Shoes finds the cleat really easily. I use the Shimano XC501 or AM7 for XT Trail pedals (Which are super easy to engage). Currently also trying Crank Brothers Candy 7 on Enduro bike, and these are super easy to engage but the float is bigger and I often heel strike compared to XT Trail. That said my two pairs of XTR PD-M959 pedals (now 20 years old) have created a reliable muscle memory and are the true hero of pedals.