I am the Desktop Connector guy at my work, and after seeing the performance for every version from v13.1(ish) to now, this crashing is intended behaviour since the beginning.
Connector makes decisions on what it's going to do "in series", and once that decision is made, it goes in the queue to try and do it "next" no matter how long it takes to execute it. For example, Connector is busy synchronizing 1,000 images you just uploaded (blue dot on tray icon), and while that is happening you rename a CAD file somewhere else in the project. Then you update that CAD file (image sync still happening). Then you rename it again (image sync still happening). Connector will have decided "I need to rename A to B" as the next thing it needs to do after those images are synchronized, but by the time it gets there, the file doesn't exist on your local PC (neither in name, nor hash ... if it even uses that), so it's probably a crash (if you're lucky), otherwise it's a loop of it never figuring out what the problem is (the dreaded "single-core @100%/consume all of my RAM "bug") which PROBABLY results in needing to reset Connector with the reset tool.
If you want to have the files always available on your PC, you have to ensure the project is fully synced first (aka: the root folder doesn't have a synchronizing icon). If it shows syncing, you need to find the offending file(s)/folder(s) that are causing this issue (there probably won't be a reason for the problem) and individually open them or do the "keep on my PC" thing (on/off maybe a few times) before Connector figures it out. Alternatively (depending on what version of Connector you have, I suggest v16.10+) you can try and use the troubleshooting button and select that project and click the "Fix All" link (if it's there) or click the "Unsynced Cloud Updates" link at the left and investigate what issues are in there. Once you have a good sync (root folder with a checkmark), turn on the "keep files on my PC" and WAIT UNTIL IT IS COMPLETED. If you don't, guaranteed problems.
I also suggest dragging the Desktop Connector icon to your active system tray area and informing users to stop doing cloud-dependent work unless it has no dot, especially the blue one; blue is basically "if something changes while I'm blue, it's a 10 minute manual process to fix it, and likely lost work". At least the red dot is "I refuse to do some things" so your local work won't be lost.
