Hello,
Seeing if there’s a way to mass import numerous songs from my iPad to ST3. I currently have them all as .txt files which would be great to keep due to the having the transpose feature accessible.

I primarily have been using TABS app with my band and this seems to be the end all solution but want to make sure the $20 is worth it

No, that's not possible as you would need to map each of the files to a certain song. So you will have to import them song by song.

Gotcha.

Is it then possible to do this via PC as oppose to ipad or iphone?

Not Pc but can do it on any OSX and iOS device
This is what I’m doing on my iMac mostly as I’m importing hundreds of songs.

It’s far easier with side by side windows with a keyboard and mouse.

And in the coming version 3.7 all your changes will automatically be transferred to all other devices.