Advice on returning to Soaring after over 20 years

Question 1: Is it unrealistic to train 2-3 flights a day twice or even 3 times a week?

Absolutely realistic, and even preferred with a quality Instructor. That's how I got my instruction years ago. Only flying once a week (as offered by the local club) would have stretched primary instruction out to several months. Instead, I soloed in less than 30 days.

Question 2: Start out in 2-33 or pay a little more for ASK/Grob from the start? (both options are available to me)

Definitely go for the Grob or ASK. You already have flight control experience. Don't waste the money on a 2-33. I realize it is the foundation of US Soaring instruction, but I refused to even sit in one. I went for the G-103 and did not have to learn how differently a "modern" glider flies from the 2-33.

In the next @140 days I would like to get to 60 or more flights.