I do not find any round more difficult to reload than any other, sticking to ammunition available to the civilian shooter.
22x6.8 has the most steps to reduce the case mouth diameter from 6.8 SPC to 22.
300 Blackout requires serious case trimming.
38/45 Clerke requires care to not damage the case when resizing it.
6,5x54 Kurz Mauser has a short case life. 7x57 Mauser lasts a but longer than others parent cases but 7mm-08 is not too bad. 7mm-08 is a bit short when first formed but grows with each shooting.
17 Remington requires some care when reloading. the small case neck causes some problems charging the case and 17 caliber bullets can be different to handle.
22x6.8 has the most steps to reduce the case mouth diameter from 6.8 SPC to 22.
300 Blackout requires serious case trimming.
38/45 Clerke requires care to not damage the case when resizing it.
6,5x54 Kurz Mauser has a short case life. 7x57 Mauser lasts a but longer than others parent cases but 7mm-08 is not too bad. 7mm-08 is a bit short when first formed but grows with each shooting.
17 Remington requires some care when reloading. the small case neck causes some problems charging the case and 17 caliber bullets can be different to handle.