I used to dive with a prescription mask, but hated that I could not see very well when I took it off, and as my vision started changing, the mask, tho had a great fit, was getting harder to see out of. I switched to contacts - for both land and sea a few years ago. I do need "bifocals", and did the mono-vision solution where one eye is near and one eye is far. It took about a week for the brain to process what is going on, but now that it has figured it out, I love it!
Both of my eyes have a pretty severe astigmatism (not as bad as some have posted here), so the multi-focal contact lenses were not an option, and I could not find a daily that would fit my eyeball shape
After many trials, I ended up with Cooper Vision XR Torics - I change them every month and I always bring an extra pair with me, just in case. You might be able to work it out with your eye Dr to order an extra set of "trial lenses" to use as your backup.
I do underwater photography, and since the camera is normally at a closer point than my near vision lens, he did order me a special near vision lens that pulled the focal point in a little closer so I can see the clarity on the camera better.
Based on comparing the glasses/prescription mask vs. the contacts, I won't go back to the prescription mask. The freedom to not have to deal with taking your glasses off and finding some place to put them - shore diving, on a small boat... As well as not dealing with all of the spots on the lenses when there is ocean spray. Definitely recommend the contacts route.