This is a complex proposal. As an avid travel I can offer ideas, but they are based in opinion, not whatever data you have.
- Seasonal - yes that should be considered. You would need some sort of date tokens to manage that with Wait Steps. Not simple to think about. There are several "birthday" threads that may help you understand better.
- Pausing - you could use the Pause feature and schedule it appropriately based on seasons.
- Lifecycle vs. Season - why not both and propensity to buy? You should have a matrix to prioritize leads, content, timing, geo.
- Geo - seems obvious that you'd have a set of Engagements by Region.
- Contract Open vs Closed - sure, quarterly and month end will create a pattern, but I'm sure the data shows people are booking meetings from Sept-mid Dec and mid-Jan through June. When should you get on their radar? July/Aug? When are budget years?
There are tons of factors here. I'd ask them why they think their model works and did they test it at a similar company. You could also ask them to plan for 1 segment, 1 geo, etc...and test that vs. Control or another method. Define the winning criteria carefully.
If you don't like their answers regarding their model, then maybe it's not a good fit.