Straddling enrollment periods, trying to get an HSA for each if possible (one is closer to Medicare-coverage)

I am too close to Medicare-coverage, with typical FSA for family (soon self and spouse),  and typical open Enroll in Dec.  Too late to build up HSA, would do one year contribution if I can figure out how.

My wife wishes to get her own HDHP and start an HSA, when open Enroll comes Aug (academic schedule).

Is there anything we can start planning for, beyond saving money for the first HSA contribution(s), would that be the max for Indv or Family for her? 

Once she gets the HSA, if family max allowed, I might not sign up for anything on my Enroll. 

Other recommendations would be much appreciated !!