Sleeping propped up really helped with the head pressure at night, but I couldn’t lie on my left side at all, even when propped up before my surgery. It just seemed to increase pressure that side of my head & set off the nerve pain too. I tried a V-shaped / orthopaedic/ nursing pillow as well as a wedge pillow & that did seem to help a bit. I presumed that the styloid compressed the IJV more?
As for your surgeries, it sounds like you have a difficult decision on your hands! We’ve had some members who’ve had the neck fusion surgery before styloidectomy and it has shifted the structures in the neck & made IJV compression worse, but then there’s a possibility it could relieve pressure otherwise- @Mcwelly wasn’t able to get a styloidectomy but has had a fusion, & I believe although it’s been a difficult recovery some symptoms have improved, here’s a recent post:
Anyone had C1 shaving? - General - Living with Eagle
Having the styloids out would be a simpler surgery to recover from, but I guess if C1 plays quite a part in the compression you might not see much improvement, & there could be the complication of scar tissue later down the line to have the C1 shaved, I don’t think I could face a neck fusion surgery though , would have to be very desperate… Thinking of you & hope you find a way to improve your sleep 
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