Hi Max,
The answer to #1 depends on the headset you end up purchasing. When looking at headsets, the features you want to keep in mind are:
1) is the headset designed for standalone play or is it designed for PC VR (if it is a standalone unit, like the Occulus Quest, you'll want to purchase a Link cable to connect to the PC)
2) does the headset use inside-out tracking, or base station tracking. Less expensive headsets, like the Quest or Reverb G2, use inside-out tracking. This means the headset has outward-facing cameras that need to see the room walls to properly orient your VR "body" and controllers within the game. Other headsets, like the Valve Index use separate base stations (they look like little black cubes) that you buy and set up in your room. I think these use IR technology, and they are generally provide better tracking, but at added cost (each base station costs around $150 if purchased separately, but can be included as part of the initial package.
At the low price end, you have the Occulus Quest 2. For $299, plus $80 for the Link cable, you'll have all you need to get started. I own this headset, and felt it necessary to upgrade to the deluxe headstrap for another $50, for better weight distribution and comfort. The Quest 2 comes with a plastic spacer to snap in between the face-pad and the unit to create more space for eye-glass wearers.
The next step up would be the HP Reverb G2, at $599. This headset comes with everything you need, no additional purchase is necessary. It has better image resolution and color than the Quest 2. Like the Quest 2, it has inside-out tracking so no base stations are needed. I owned a Reverb G1, and liked it generally (I bought corrective lense inserts) but found hardware build quality lacking. My unit failed and was replaced under warranty, then the replacement unit failed after the warranty expired.
Next level up would be probably the Valve Index, at $1000. This unit uses base stations for tracking and offers at wider field of view than the previous two headsets, however the image resolution is lower per eye. Its a solid unit but its drawback is the lower resolution. You will probably need to use the zoom feature to read cockpit gauges.
HTC makes one called the Vive Pro 2, which has similar image resolution to the Index but better screens - AMOLED vs LCD. so the colors should be more vibrant and the blacks darker. A full kit costs $1200 at the HTC store.
I think most headsets have enough room for eyeglasses but I would look at YouTube reviews of headsets to see what they say.
I still recenter my view fairly often. I have a button mapped to my stick to do this. Its a habit now so I don't find it off-putting. I think its because VR is such a "real" experience, my body and head positions change depending on what's going on in game - for example I frequently find myself 'ducking' when the virtual a/c pass too close for comfort.
