Hi all - OP here. The work is finally done! What really drove the timeline is that our A/C was not blowing hardly any air to most of our rooms and it was not very cold. I just feel the money being spent on running that A/C just going up in smoke.
Agree with all that venilitation really important, but also I had a lot of gaps between my main floor and attic that were no doubt causing the attic to be so abnornally warm.
I bought a white plastic work suit for 10 bucks , a good mask and got to work. I ended up navigating around my attic and sealed all the ductwork (some of my AC ducts were not even attached to the main ductwork in attic - so we were blowing cold air into the attic rather into our home). I sealed holes in flooring. I learned that my bathroom vents were not vented externally in first place so got that done (thank you, Youtube!) using insulated duct to avoid condensation. Luckily, no damage due to that issue (ventilation was not previously used much, but it will now!). I removed and added new flexible duct work for A/C where the duct insulation was missing. Even made sure my kitchen vent was going outside (again, also major holes between main floor and attic , as well as from vent to roof). I did contract out the final soffit work and the blown-in work, but did nearly all prep work myself. I now have about 18-20" up there now (R49+). I did so much prep work but super glad I did it myself because I could check in on the guys doing the blown-in and they could tackle the things I couldn't (I am small female). I was able to double check their work and remind them of what to do so I know that saved us money rather than just waiting downstairs for them to finish ignorantly. I think we saved about 3k from my first, all encompassing quote.
I just could not believe what shoddy work had been done before (almost certain it was hired out since previous owner would have been 90 years old when HVAC was installed).
Thanks everyone for your comments. Fingers crossed for no ice damning next winter.