My buddy got caught in one on Elbert, now he's off the summit by noon too.

Maybe one more winter" is inspector talk for "I can't promise anything but it looks okay from here." Those guys cover themselves because they don't want to get sued, so they always give you the worst case. A 900 sq ft roof is small, like 12 or 13 squares, and that 8k number sounds like a full tear off with fancy shingles. On a cheap house you can do a layover or just patch the bad spots for way less. Get a couple actual roofers up there before you panic, they'll tell you the truth in five minutes for free. If it's just worn shingles and no soft spots in the deck, tarps plus a patch might buy you years. But walk the attic yourself and look for stains, because the inspector isn't the one paying for this place.