It’s very seasonal here and the only months I’m actually paying the mortgage in full is during high season in summer.

That fills your unit for the winter and buys you time to prepare for the next time.

Is there a peak season, or does Gulf Shores have a consistent flow of visitors year-round?

I created these riddles for seasoned investors.

My problem is that every six months I have to move (summer season North Carolina, winter season Florida) so I can't use first home trick.

You won't likely see an influx of renters though unless you did a short term rental during the winter season when the outage happens down there.

Is anyone doing MTRs in the North San Jose area and using their property both for STRs and MTRs within the same calendar year based on demand, seasonality, etc.?

It sounds like you will actually occupy the home in Washington for a majority of the year, and then travel to Aspen during ski season.

It's usually better to earn $200 less a month for one year than to sit vacant for two months, particularly in the winter.Consider a bigger drop for a 6-month lease to get through winter, then increase rent or find a new renter in the spring when competition is hotter.

Also, do you tend to give lower rental rates in the winter months?