I have found that prioritizing technical debt is much like paying down financial debt. The idea is to prioritize from smallest to largest, and snowball your gains into tackling larger debt. Once you solve the smaller issues one at a time, you will gain steam and acceptance from management to tackle bigger issues. They will gain confidence in your plans as you prove successful in smaller issues. Just make sure your smaller successes actually fit into your plans for larger issues.
I have found that prioritizing technical debt is much like paying down financial debt. The idea is to prioritize from smallest to largest, and snowball your gains into tackling larger debt. Once you solve the smaller issues one at a time, you will gain steam and acceptance from management to tackle bigger issues. They will gain confidence in your plans as you prove successful in smaller issues. Just make sure your smaller successes actually fit into your plans for larger issues.
That's great advice! Start small, see some good successes and have data you can point to, and keep moving onward and upward.