On Thursday, November 16, 2017 at 9:33:13 AM UTC-5, Michael wrote:
I am finally returning to Soaring after over 20 years, I earned a Private Glider rating in '91 and had @175 flights in 2-33/1-26 and a Private Power rating in '92 and 350hrs.
My goal: Regain currency/proficiency and purchase a standard class non-flapped glider.
Specifically I was looking for advice/opinions on how best to proceed to that goal in a short time frame (140 days)

Question 1: Is it unrealistic to train 2-3 flights a day twice or even 3 times a week?
Question 2: Start out in 2-33 or pay a little more for ASK/Grob from the start? (both options are available to me)

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

The glider you fly is much less important than the quality of the facility and instruction available. There is value in flying more modern trainer, but this is commonly over stated. Flying a few different ships exercises basics in slightly different ways.
Having flown with lots of returning lapsed pilots my observation is that getting in the seat flying skills back may not be all that hard. Getting the knowledge back, and current, is harder, less fun and interesting, and hugely important. This is particularly true for someone who will not have to take a new practical test with and examiner.
Good luck and welcome back.
UH