I've been using Quicken since 1996 and over the years life has transitioned and changed. The number of stored transactions causes slow searches and its just cumbersome with all the categories that are no longer used. I'm thinking of starting over at the beginning of 2027 with a clean file. I plan on doing a clean up between now and Jan 1 of checking, savings, and credit cards so that will be far simpler. Property and debt isn't an issue. My biggest question is hints on how best to track investments in Quicken. I'll have the opportunity to set each type up as a new account so it would be ideal to do it right this time around. Any thoughts and hints would be appreciated. I'm in Quicken for Windows Release R69.53. Of course the downside is that I may/will lose the history going forward but I'm willing to do that.