July or January is when most new headcount comes online. Company shuts down for most of July and August so that's a good time to ramp up. Bonuses are pro-rated so doesn't matter comp wise. If moving to Seattle area, may be able to get a better deal on rent in winter vs August/September when everyone moves here
Good point. Stayfit is only $400 if join past a certain point in the year. Has to be spent in the calendar year. HSA credit is also reduced for starting past a certain point. ESPP enrollment is quarterly and contributions are per pay period so maybe join before the start of a quarter but probably not worth optimizing for
Before considering MSFT, ask them about: 1. Their time off policy 2. Remote work policy 3. Flexibility of commute hours
Also keep in mind that one thing is what the recruiter tells you and another thing is what your team does. Ask the colleagues of your future team how they feel about the points above. If you are based in PaloAlto and considering relocating to Redmond, WA, try visiting the place between Nov-March and see if you fit in culturally and weather wise.