What are your actual dates?
Flights for spring 2020 on SW are likely going to be released between July and September of this year. The next SW release on June 20 takes us out through early January 2020 (so you can see how flights through March/Apr/May could be released quickly thereafter). If you're traveling during the busy spring break period, you probably will want to jump on those flights quickly.
Why are you advocating for a SW Companion Pass? Do these people fly often? If this would be the only flight where they'd use the Companion Pass, it could be overkill to focus on it out of the gate (considering it requires 2 cards and additional MSR).
I think for anybody to give good advice we'd probably need to understand each of the following items:
- Exact Travel Dates
- Makeup of each family unit (# of adults, # of children per family unit)
- What City (or cities) would they be traveling from
- Are you all planning to pool and share points or does each family unit need to earn their own way with their own cards
- Regarding the CP, do any of these families travel via SW at other times in the next 18 months or would this be their only flight?
- When you say "we can do biz apps" do you mean that EVERY adult is willing to pursue a biz card and can claim a qualifying biz activity? I never like the word "we" in this stuff because sometimes "we" means certain people and not all people, lol!
It might be hard for you to give "one size fits all" advice to your family. Each of them might get their own set of instructions based on their specific situation. The good news is, if you hold a CSP and CIP you could get a lot of support points out of this!!