Matching Calibre library to Kobo

[HFM1101]

Hi, I need help please.

I've just bought a Kobo Libra Colour - it's my first time buying an ereader outside the Amazon ecosystem. It's been a while since I've messed about with plug-ins and computer stuff, so I'm a bit rusty, and I definitely don't know how to do command line, so just letting you know my level here.

I have 2 problems.

1. I want the books to appear on the Kobo in the order they are in Calibre. They show on the Kobo as alphabetical, even when I click on the filter 'date added'.

I should say that I copied and pasted my azw3 library to the desktop, then with the original library still in Calibre, I converted to epub, and from there the books transferred to Kobo in the kepub format. Is there any way to make Kobo match the order of books as it is on Calibre?

2. After I downloaded library, I ran into the stretched covers issue, and I'm of the understanding that this is caused by the SVG covers and I'll need to go into the output, select 'No SVG covers' and convert them all again.
What I'm not clear about is if it's OK to convert from epub to epub again (do files degrade in any way by doing this?) and once that's done, how best should I put them back on the Kobo - do I need to delete the whole library on Kobo and then transfer 20 books at a time (any more and everything freezes - it's a 1000+ library)? Or do I not delete and just drag and drop the whole library onto the device and hope just the covers get changed? I've never been clear about this, even when I used Kindles. Would this action simply overwrite, or would I be creating two copies of everything?

Many thanks.