JohnBurke

At no point in that evolution will he be working just 9 months a hear, leaving three months of consecutive time off work.

Conversely, the greater one's seniority, the more time off. It just wont be three months continuous.

NYC Pilot

The 3 consecutive months off is an entirely different story, highly doubt that can happen as an airline pilot.

Panzon

Alaska: there was a little seasonal work for low time pilots in SE, but, as I recall, that company recently went out of business. I know the seasonal float operators in SE and Lake Hood are lowering their minimums but are still looking for some Alaska time (i.e., these are not entry level jobs). Occasionally on Craigslist I've seen lodges looking for wheel plane pilots and some of them have low minimums (but lodge flying is usually best suited to experienced pilots, regardless of the lodge's minimums). This type of flying has the potential to make a lot of brief acquaintenances and a few deeper friendships.

Firefighting: has already been mentioned. A friend in the business tells me there will be a number of lead plane openings this year. You could go to next year's training/conference (can't remember the name) to get your initial classroom work done and to network. My friends in this world liken the friendships to a tight fraternity.

Ag: work is seasonal. It used to be that a guy would start out as a loader and work his way into a seat, but I think the path is accelerated these days. Takes a lot of skill, concentration, and endurance, and could be enjoyable work. My friends in ag don't seem to make a lot of acquaintances during the season - they're pretty much working until they drop day after day.

There are small numbers of corporate / high net worth individual gigs that are seasonal. These jobs definitely require being at the right place at the right time, and it would be hard to define a path that would have a high probability of getting you there.

These are the only seasonal jobs that come to mind, although I'm sure there are others.

Some of the Alaska operators offer 2 on / 2 off schedules. It's obviously not the same as working seasonally, but maybe it would have the same net effect for you.

Scraggly Heron

There's a path to something like the OP is talking about, although it's not necessarily the flying career that most would want:

1. Continue to build flying hours
2. Get a job with General Atomics; they are one of the few companies that will hire someone without a clearance and then pay for the new hire's clearance. (Note--there's a reason for this)
3. Apply to the ISR companies, e.g. L3/Javaman. You'll be gone about 6 months out of the year total, I believe it's 2 months on 2 months off. However, when you're home you're not working. Live wherever you want.