Help organizing and submitting documents to prospective lenders

[Matthew Pinkston]

Hello all, 

(TL;DR version): How do you organize and submit documents to a prospective lender? Additionally, what's your process to keep those documents up-to-date?

I'm in the process of finding a portfolio lender to help me finally purchase a 5th buy-and-hold property. I've gathered all(?) the documents requested by the first lender in a folder on my desktop. 

- last 2 years tax returns
- pay stubs
- pages and pages of financial account statements (bank, retirement, brokerage, etc.)
- driver's license, ssn
- mortgage statements
- ???

The list goes on.. But my problem is with keeping all this organized, up-to-date, and presentable. Is it enough to simply zip up the folder and send it off, or is there some expectation of bundling it all in a more digestible format? What system do you use to keep such a large number of documents manageable and ready to be put in front of a prospective lender?

Any advice would be greatly appreciated!