Why not? Is there a disadvantage outside bad smell?
But the real reason is that you are carrying enough energy to carry you, 4 of your friends, and 3500# of automobile 35 miles away in a container not designed to avoid spillage, venting vapors, nor survive a collision. (That "aside from the bad smell" is dangerous, both to mammals and from an explosion risk perspective.)
Rotating the gas is easy.
Snark aside, if people have a hard time remembering to refuel then there should be some technology to remind them. Something as simple as a phone reminder would do the trick.
2) Research your fuel tank capacity (Also a google-able event)
2) Fill your tank completely
3) Reset your tripometer; drive until it nears the magic empty number: (Fuel Tank Capacity)x(Adjusted MPG). When it's within 10% of that number, you should consider adding more gas. If it's even closer to that number; you should really considering adding more gas.
4) Reset the tripometer every time you fill up
(You're also leaving the path of "saving money" vs fixing the gauge or just using 1/2-3/4 of the factory tank using ded reckoning by trip odometer. Typical fuel cell at Summit Racing is over $200 plus plumbing parts needed plus installation labor.)
https://www.livescience.com/58117-does-gasoline-go-bad.html
Ask anyone who has ever left untreated gas in their lawn mower over winter. It takes a drain and some work to get the mower started in the summer. Throw in 1oz of fuel stabilizer, and all is well.
(So the obvious answer is to put fuel stabilizer if you are going to store gas for > 6 months. It only costs a few cents per gallon)
They do have gas problem every year with their snow blower, it's systematic, they just don't put enough care about it.
Is there anything about the generator that could have helped? Is there's fuel stabilized that can last a decade? We were pretty happy to see it start such "easily" and be able to plug our essential stuff on it without having to go buy gas.
If it's a portable generator, either put 100LL in it or (even better) run it entirely dry (to shut down) when done using it.
To your stable fuel question, for a permanently installed unit in a residence, I think it's incredibly hard to beat natural gas as a fuel supply for it.
It's pretty common for home generators to be natural gas. If gasoline, maybe keep the gas outside of it and rotate it every 3 months. I.e. have a 10 gallon can of it you buy in Jan. In april if you haven't used it yet, use it to fill up your car, and buy a new 10 gallons in a can. That way your gas is at most 3 months old, at the cost of having to lug around a can 4x a year. You could likely reduce to a 6 month rotation and not have much difference either.