I do snow removal also. Last year was terrible and ran through all my savings to get through winter. I was miserable lol. This year I'm trying to save more and pray for more snow. Getting a winter part time job if you have connections is a good idea. Other than that if you know any other trades your gonna be slow. Maybe you should keep a job through the winter to protect your self after all your new investments, Good luck.
Byron Smail Landscape Contracting
Design/Build/Maint. Snow Removal, firewood