What kind of pedals do you have?
I have Look Keos FWIW. It took a fair amount of time to get the feel of clipping in down, and I still have days where I seem to fumble around a bit. It's easier if I hoist myself into the saddle at the right time as my pedal is moving forward. For the time being, I would suggest going to a parking lot and just practicing clipping in over and over again. It does get easier. It sounds like you're already well ahead of the learning curve b/c of your past use of toe clips.
As for your foot numbness. It may be a function of your cleat placement or a function of your shoes or both. My fitter set my cleats up as part of my fitting, but I still get a numb big toe on long hot rides for whatever reason. We'd done any number of things to address it, with limited success. I've decided that it has something to do with some past injuries to that toe.
Anyway, a lot of shops offer a cleat fitting for a somewhat minimal charge. It's not a bad thing to look into because if your cleats aren't positioned correctly, you can encounter knee problems.
Live with intention. Walk to the edge. Listen hard. Practice wellness. Play with abandon. Laugh. Choose with no regret. Continue to learn. Appreciate your friends. Do what you love. Live as if this is all there is.
--Mary Anne Radmacher