Your story sounds like the experience I thought I'd have. There'd be certainly a lot less difficulty if the equipment I got just captured accurately right out of the box.
I agree with you on the value of making supercuts of the clips. I've made two video montages from my videos, and those are the clips I most often re-watch.
Thanks!
Although presumably they don't do audio...
When digitalizing VHS tapes, generally one doesn't have a HDMI signal to use. They either have Composite (typical) or S-Video (better, but rarer). Typically, one should get a Composite/S-Video to USB device rather than trying to add a Composite/S-Video to HDMI device into the link here. Adding more pieces that you don't have control over tends to result in more issues and/or worse capture quality (due to extra filtering/compression steps applied).
Devices like the "Hauppauge 610 USB-Live 2" and "Elgato Video Capture" (I'd use the Hauppage device personally) provide a Composite/S-Video to USB 2.0 adapter that can provide uncompressed video.
The capture part was easy enough, did it over a single weekend. I bought a camera that could play the tapes (~$100) and an Elgato Video Capture (~$80). Quality was as good as possible from the tapes and no audio issues. I also did not want to use a third party because I was concerned they might botch the job / lose the irreplaceable tapes / etc.
The editing took about a month, I've never done video editing before. I just loaded up stuff in iMovie and grouped stuff together as it made sense to me. Most of the time was spent just watching the videos (I think I had around 60 hours of footage) which was enjoyable and necessary.
In terms of sharing, I paid a friend who does video editing to make a supercut of all the best moments and I screened it at the family Christmas (many laughs and tears). I gave folks thumb drives of clips that were specific to them, but honestly I'm not sure if people even watched them. The movie format made it more digestible.
If anyone wants the Elgato, I still have it and can give it to you for the cost of shipping. Also happy to refer you to my friend for editing needs, he's very affordable.