I've been planting winter and crimson clover mix or something of that variety for around the last 5 years usually let it go fallow till late summer then Bush hog, spray once sometimes twice with gly a couple weeks apart and then drill
I don't have any experience with crimson clover, but I'm guessing by the time late summer rolls around crimson is probably about done and dried off too?
If that's the case, try skipping the spraying for a year or two, and just plant right into that standing dead crop, then come behind it and just press it flat. Don't even mow it. If you're spraying even once, and especially twice, you're looking at a minimum of 14 days or weeks longer of nothing growing. When all is dead like that, you lose all of your soil's glomalin. Glomalin is what holds your soil pores open, it's the plaster holding up the ceilings in the tunnels.
I'm not anti-spraying, but take a good hard look before you do. If you don't see a massive flush of weeds coming, skip it, and then delay it as long as possible.
And don't forget the chicory. The longer you can go without losing your glomalin, you'll get ever more and more aeration from worms and other soil critters that bore holes and channels. The disc will only give you the illusion of breaking compaction. Soon after, you'll be even more compacted, but now down a few inches.
Here's a 60 second read on glomalin with more big words.
Glomalin, the substance coating this microscopic fungus growing on a corn root, can keep carbon in the soil from decomposing for up to 100 years.
www.sciencedaily.com