I’m building a new personal PC and planning to migrate over all my data drives. Across 6 HDDs and SSDs, I’ve got about 15 years of digital clutter across wildly different *file organization practices*. Some drives are semi-organized, others are just pure chaos.
The plan is to consolidate everything down to 1 or 2 clean drives and wipe the rest (yeah, I know — deleting data is heresy, but I’m trying to be better).
I'm thinking of writing a script that:
-
Crawls each drive
-
Filters for specific file types (starting with Office docs, maybe PDFs, code files, etc.)
-
Moves them to a clean drive in a sane folder structure
-
Optionally does deduplication (because I’m sure I have the same files copied across multiple drives)
I'm not a stranger to scripting, but I’m wondering if any of you have tackled a similar cleanup. How did you approach it?
-
Are there tools you recommend for this?
-
Any good dedupe strategies or software?
-
Would you go full manual, visual, or automate as much as possible?
Would love to hear your war stories or lessons learned.
P.S. - I used chatgpt to organize my thoughts on this and I'm sorry.