Thanks for all the hints.
I tried to change one thing at a time, to better know what the problem was.
First I messed with the leather straps on the pedals. I untwisted one section and raised the buckle. I think the twist was there to keep the strap from migrating around but I wanted every bit of slack available. At this point, getting into the pedals was physically possible but I needed to lift the cage with my hands to clear the cleats.
Next I removed the front Velcro strap and put the laces back. The laces were only out to keep them glue free for a recent trip to the cobbler.
This had two minor changes that added to something big. First, the strap can hang up, so I'd have to force into the pedal. This didn't happen a lot in my monkeying around but it's on the right track. The second change that was kinda huge was that the Velcro was bolted to the bottom of the shoe, under the cleat. This made the cleat angle up more. So the forward edge of the cleat was already a bad ramp, this made it more of a wall. With this gone, it became possible to get in and out, though still a pain.
I may grind the cleat into a gentler ramp.
I've got the bike on a trainer to mess with angles and I think I've got it.
To the people who suggested filing out the groove or cleat covers because of wear, had you read or looked at the pics, you'd have seen a nearly new cleat. Possibly an issue in the future but certainly nothing to do with the current situation.
I'll have an opportunity to ride tomorrow, I'm a little nervous about a big day with zero float but I'll try it.
These are pretty comfy shoes, long term I'll probably put Keo cleats on them, once I've gotten my jollies from the toe clips.
Maybe I'll clean the garage next
