If you want to focus on improving your barbell bench I'd: Drop the Smith Machine completely, just forget about it. Focus on barbell benching. Drop either the military press, or the dumbbell press. Replace that slot with a bench variation (paused/pin/band/chain/long pause/board/etc), so that you're benching at least 3 times a week in some form + doing some other press work once a week (DBs or military). Pick a bench variation and stick with it for a few weeks.
Your singles can benefit from being practiced. Doing nothing but AMRAPs and sets of 8+ and then trying a 1rm out of the blue is probably not gonna cut it. You need to be lifting in a zone that is closer to your max. Think sets of 4-6 for volume, and regularly schedule a single at 90% or RPE 8 at the beginning of your session. Try not to fail sets too often. There's other ways to do it, but that's one.
The overall takeaway is that you probably need to do much more actual benching (not Smith) and less of other stuff, and that you need to work in a zone that is closer %wise or RPEwise to your singles, while still getting enough volume, if you want to get better at singles. How much volume is appropriate should be determined experimentally, but 3x a week, 4-6 sets a day with some singles thrown in can be a good start. Look to avoid grinding and failing sets too often, while adding 5lbs when you can from week to week, and leaving 1-2 in the tank most sets.
The reality is that you'd benefit from an actual professionally written program, complete with peaking protocol, etc. But I think that alone will improve your results. Basically any reputable bench/powerlifting oriented program will give you massive gains compared to what you're doing currently.
