Running old Program (RideRunner) designed for older Windows versions

Settings: UAC off, Installed as Admin and being run as Admin. I even tried compatibility mode with no luck.

I have this program called RideRunner for a CarPuter that plays music, Navigation etc (much more than that but you get the idea).
It was developed when XP was out but was still updated for Windows 7.
Now with Windows 10 I have a couple problems getting it to work like in Windows 7.
That forum is pretty much dead so I am hoping to get help elsewhere.

In Windows XP and 7 after shutting down the computer and turning it back on, it would resume to what you were playing and the exact time the song left off at when it was shut down.

Windows 10 will not resume where it was left off. The program opens but does not resume the music where it left off. I don't wan't to use hibernate as a plugin that I want to use don't like hibernation.

1: What changed in the shutdown or startup process between these versions of windows. I was hoping to troubleshoot myself maybe.
Any other ideas to check out?

2: Windows 10 does not like this program at all, as the only way I can get it to startup when Windows starts is to add it to the registry. I tried the startup folder, scheduled task with no luck. But there is a 10-15 second delay before it starts after seeing the Windows desktop. I was also wondering if this could be causing the first problem.

Is there a way to make Windows 10 trust I program it don't like so I can just put it in the startup folder and maybe it will load faster without the 10-15 second delay.

Any help will be appreciated.
Thanks

"It was developed when XP was out" may be part of the problem, only WinXP Professional was available as either 32-bit or 64-bit and you may be running the 64-bit version of Win10.

It ran in 64 bit Windows 7

If I close the app before shutting down Windows it works correctly but if I let Windows shut it down when I press power button it does not work. When the app closes correctly it creates a resume.ini file that it loads when it starts back up but this is not being created.
My guess (but don't know too much on this) is that Windows is killing the process and not sending a request to close the app causing this problem. The app is not hanging as Windows shuts down in a few seconds.

Is there a way to create a script or something that will close the app when Windows gets the signal to shutdown?

Any suggestions?

Thanks again.