Can I update I update my 4th generation iPad to 14.4?

Yes.

Click on this link to read how to "Update your iPhone, iPad, or iPod touch" --> https://support.apple.com/HT204204 - When you try to update you will only be given one update selection which will be the highest available iOS version supported by your device. If it says the device is up to date and you need a higher OS version you will have to buy newer equipment.

No. Its CPU isn't powerful enough for 11 or above.

(191150)