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Do you have a hard time reading on the Voyage you currently have? I don't know that the iPad would be any easier to read, but the font sizes are adjustable within whatever reading app you're using, and the screen resolution on modern iPads is great.
The short answer is no, you cannot simply connect the iPad to your computer and transfer the .mobi files to the iPad directly. There are several ways to go about getting them onto the iPad, but none are "drag-and-drop" type operations.
You could install the free Kindle app on the iPad for reading the .mobi files without conversion. To get the files into the app, you could import your enitre library into Calibre and have Calibre automate the process of emailing all the files to your device, using the asssigned email address of the Kindle for iOS app. Or you could put all the files into a cloud folder, such as on Dropbox or Google Drive, and navigate to them one by one using the corresponding iPad app. Then you select each file and select "Open in Kindle." That would be tedious for several hundred (or thousand) books.
Alternatively, you could use Calibre to convert all the .mobi files to .epub and use those on your iPad. MapleRead for iPad can connect to your Calibre library wirelessly, if you turn on the Calibre server using the application on your computer. Navigate to the Calibre library using OPDS in the MapleRead app.
If you had a Mac computer, you could use iBooks with iCloud and import the .epub files you converted using Calibre into iBooks. This would upload the files to your iCloud account, and sync across all Apple devices logged into your iCloud.
Hope this helps,
JD
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