I've thought about this as well, and continue to do so. I've really come to enjoy scanning & finding new signals so my scanner collection is growing.
I started with ProScan to automate recording received signal meta data and audio recordings. The capabilities of ProScan are fantastic and has taken me a long way on my journey. I continue to utilize ProScan from time to time. Using it with more than one scanner at a time though didn't quite fit how I wanted to work. I absolutely don't view this as something against ProScan. Rather, how I want to utilize my scanners doesn't match what ProScan excels at.
I've been working on developing my own Scanner Software that specifically focuses on interfacing with multiple scanners at the same time. As an analogy, I'd put forth what the Data Center / Server room industry has done. Moving from single application on a single server to cloud computing or other clustering techniques. Like ProScan it records/logs/shares meta data on received signals and also records the associated audio and saves it to a file system.
In terms of File management, everything gets saved to a mapped network drive on my NAS. A typical folder structure is used to manage the date/time, system, and individual files. For play back, I simply use a media player( VLC, Windows Media Player, Audacity, etc ). I think there is opportunity for making this a little bit better, but haven't gotten that far yet.
I think I'd like to disclose more about my software project in the future, especially if there is interest from fellow RR members who have have "too many scanners" and "not enough scanners" all at the same time. Its still pretty raw right now and want to get a little bit farther before doing so. I've demonstrated to my self the approach & concept works and better matches how I personally want to utilize my scanners.