Calibre takes various liberties in the conversion process which may or may not suit you and may or may not keep amazon happy. Many of those can be changed with options and settings.
You might want to consider borrowing a kindle reader or buying one used or new. But each firmware version and each hardware model behave differently.
To see what calibre does in each direction, you can convert an EPUB to KF8 by both calibre and kindlegen, then convert both KF8 files to EPUB by calibre and kindleunpack (giving 4 secondary EPUBs. I think you will find that kindlegen -> azw3 -> kindleunpack comes closer to the original EPUB than any of the other 3.
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