How can I transfer music from a flash drive like leaf bridge to my iPad Air and then have that music stored in iCloud?

Simply replace "external drive" for "computer" in these instructions -
https://macroplant.com/iexplorer/tutorials/how-to-transfer-music-and-playlists

I've uploaded pictures to iCloud and they have still been on my phone after the upload. I've also done the same with Amazon cloud services and the pics were in both places.
The iCloud is like a spare hard drive, all you do is copy the info to the cloud so it's available to download somewhere else when "you" log in....

You will have to remove pictures, videos and apps that you are not using any more. You can sync the ipad to a pc or mac and save the pictures and videos you want.The icloud is tied to your apple id. go to this link ( iCloud ) and sign in with the same info you use to sign in to the app store. The icloud gives you free online storage for pictures videos and documents that you have on the ipad.

The apple store is great help in this area. Apple is a little complicated. Their Tech's are very helpful.

Hagd!

First, Plug your iPad into your computer using a iPad charging cable, iTunes will usually by default open, just hide the window,, as well an AUTOPLAY window should open, find where you can see "open folders", click, Windows explorer will show an internal storage image file, double click the internal storage image, you should see a folder called DCIM, double click the DCIM folder. Once open, you should see several folders with funny numbers and letters, they make no sense, but, this is where images that were either, captured by camera or, from the iPad desktop capture feature will be stored, along with any other software that has the ability to capture an image and save it to the camera roll. You can open a folder or select one by clicking once on it, then press CTRL & the letter "?", this selects all the folders, the press CTRL & the letter "C" this will copy all the selected folders, then open your pictures folder, or where ever you'd like the images saved, press CTRL & the letter "P" this will now paste all the folders with the images from your ipad into the location you have selected. Done! Alternately you can sync your iPad, however you must first select the correct setting within iTunes to sync to the correct folder, as well you can turn on iCloud Drive and sync your photo's to the cloud system, which leaves a folder with all the synced images inside the iCloud folder. I hope you have found this information helpful, if you have please leave a positive rating. Good Luck!

If you have iTunes installed on your computer you can back up all your apps and data on your computer. Then you should be able to plug in your new iPad air and migrate all the data to it.

The best way is to use a transfer tool, this one works well:

How to Transfer Movies from iPad to PC Mac Windows 7 8

just istall iTunes software from Apple and plug the iPad connector cable to an USB plug on the macbook.
then turn the ipad on and start iTunes - you will see your iPad in the middle on the left side of the screen - then it prompts you to sync
Apple iTunes Download iTunes Now Apple iTunes Download iTunes Now Sync your iPhone iPad and iPod with iTunes using USB

You can choose iTunes to sync iPad with your Mac, but you should be careful when you are using iTunes to sync iPad. iTunes is not simply backup or transfer software, and it doesn't allow you to transfer non-purchases. So you only have authority to sync purchased items, including apps, music, movies and so on to your Mac or iTunes library. Check out the following steps.

1. Authorize your new computer to use your Apple ID. Install iTunes on your new computer and then Authorize it in the Store tab.This is the email address you use to sign into iTunes (and probably anything else Apple-related). If you don't know it offhand, you can just check the computer you're currently syncing with. If you go into the iTunes Store it should appear in the upper-right corner. Once you know it, go to the new computer you want to sync with and locate the Store menu. From there, choose "Authorize This Computer". (In the event you've switched Apple IDs and made purchases with more than one, you'll need to perform this authorization for every account.)
2. Back Up Your iPhone. Just in case anything goes wrong when you are syncing, back up your iPhone, so that if all else fails, you'll be able to restore it to the way it is right now. To do this, connect your iPhone to your computer with its USB cable and open iTunes, Click "File > Device > Back up".
3. Transfer Purchases from your iPhone. Now you'll want to transfer all of your iTunes purchases (including free apps, paid apps, songs, books and movies) from your iPhone to your new computer. To do this, right-click (CTRL-click on a Mac) your iPhone within iTunes and choose Transfer Purchases. Or click "File > Devices > Transfer Purchases from my iPhone". Then iTunes will start syncing the purchased items to the library.

http://www.leawo.org/tutorial/how-to-sync-iphone-to-new-computer.html