There are possibly "known problems" with System Restore on some recent Win 10 releases, I've had the same happen on a newer Win 10 laptop of mine. If you click the Start and type "Winver" (winver.exe) and then Enter you'll get a dialog box that shows your Windows 10 version.
Wombat666 is probably suggesting a more reliable way to protect your system. My opinion is that I don't think Microsoft is going to get their situation with Windows 10 sorted out any time soon. An external drive or two are a bargain for keeping things simple.
If you haven't checked out "tenforums.com", "eightforums.com" and "sevenforums.com" yet you'll find a clever and sympathetic group of people who share many similar problems with Windows.
The system of mine that won't complete a restore is a Win 10 1709 version. A few Windows forums suggested that permissions on the "bootstat.dat" file under \Windows folder are incorrect and System Restore can't access the file (see your screen capture). The fix was to boot from a DVD or USB drive -- this system dual-boots Linux Mint 19 so I used that -- and rename the stuck "bootstat.dat". This worked OK for me and the restore completed to the restore point, but I don't know yet if I have to do that every time I do a restore. That's non-critical on that system so I can continue to try things without having to actually depend on a restore.
I'm like you, I used System Restore all the time on Win XP and Win 7. Now it may be a "known problem" on some Win 10 versions according to some of the community discussion. Update to Win 10 1803 or 1809 break a custom application I use on that system, so if updates fixed the problem I'm kind of out of luck.
I'm starting to think my "next" Windows 10 system will be stripped down to just the Microsoft "Hyper-V" virtual machine and then I'll run a nice stable Windows 7 on top that doesn't obliterate itself with automatic and quasi-uncontrollable updates.


