Weather can be a problem at any time of the year. You've got 3yrs of exam credit, so just get on with it. Ice is the biggest obstacle during winter, but chances are by the time you've done the CPL bit it'll be summer again.
I seem to be less "vinegar stroke" than others about G1000 aircraft. Whilst they are obviously a big step forward, I'm perfectly comfortable with a 6 pack for instrument flying so not particularly bothered either way. Perhaps it's just the way my brain works. That said, I did get mildly excited the first time I flew something with SVT in the states.
I sincerely doubt airlines will give 2 hoots about you having "cut your teeth" on steam gauges. You won't be seeing too much of them flying airliners.