I worked for a place where if the decision was between spending X hours now, or spending an unknown number of hours that would be likely to be 5-10x hours at so

I worked for a place where if the decision was between spending X hours now, or spending an unknown number of hours that would be likely to be 5-10x hours at some indeterminate point in the future, they would _always_ kick the can down the road. I can't figure that mentality out, when I would regularly predict trainwrecks and then say, "I told you so." when I turned out to be right, and yet, no one would listen to me. "Here's how you can avoid this being a problem in the future." was another thing no one cared to hear. The only way to fight technical debt was to do it in your spare time, in secret, and then announce it when it was done... and I'd talked to others who had the same attitude (including a manager). I can't figure out how a company with that kind of culture could stay in business, but it did. I think the only thing to do in that kind of situation is your number 2 option.