Yep. I've found that the ticket or tech debt isn't important until it becomes on fire and must be fixed ASAP. It doesn't matter that the possibility for the bug to happen has existed for 2 years, the organization doesn't find the investment worth it until it's burning down the house.

which seems like such a blatant failure of leadership. If I had 1000 ways that I could invest $1000 at a 20% return this year and like 5% recurring[1], why not hire 2-3 engineers get them done and keep the extra $200k plus have a better future?

The most compelling argument was opportunity cost against features (eg the time spent on feature work would return 100% per year or whatever seems enticing) ... That seemed to me to only suggest we should do _both_ (get more capital in the market if required)

[1]: some amount of recurring makes sense so long as things like customer retention, brand value, maintenance costs are factored in

I feel like the dynamic still holds true. If the team was underfunded two years ago, and still underfunded one year ago, they will probably still be underfunded with regard to tackling the problem now. The ROI argument seems similarly dubious since it might hold true for things with high upfront costs but otherwise if the perceived ROI had been high then a team short on resources would have already prioritized it.