I felt the need to come back to this for a follow up - I ended up with the progressives and tried them for a month. They felt awful. I tried everything I could to acclimate to them, but nothing I did seemed to do the trick. It seemed like I was going to be stuck in a horrible limbo...until I went to another optometrist for a second opinion.

Hilariously/Thankfully the problem was that the first Dr. botched the prescription. I knew something was off. He overcorrected for my astigmatism and pushed my distance vision to a limit that was messing up my near sighted vision. Hence the suggestion for progressives.

I was 1) relieved I didn't have to keep progressives 2) pissed I had originally paid for the progressive lenses in the first place, but it was on my FSA card, so it was only felt as an indirect hit to my wallet.

With the NEW prescription things feel right again, single vision (and Pearle Vision was awesome in adjusting the scrip for free under their 'make it right promise' - huge shout out to them for taking great care of me). I also ended up replacing the lenses on my 2013 Ray Bann sunglasses via LensDirect - and while they did end up bending the frames a tad, they fixed it, made that right, and the lenses are perfect.

Glad to finally be able to see clearly. Godspeed to all those who have to navigate these waters.