The amount of places you attempt to do with such a short time is mind boggling. You will probably be on train most the time without any time to explore the places you intend to go.
That said, my trip to Hokkaido is next year, but your round 2 is rather similar to my itinerary but in steroid version.
Have you checked the journey on Hyperdia? Hokkaido has no Shinkansen so traveling time is a lot longer as compared to main island.
Eg. Sapporo to Abashiri is about 300minutes + trip assuming you do not make any side stop on the way, trains are not as frequent in Hokkaido as main island too, eg. Sapporo-Abashiri 7:21Am OKHOTSK 1, next OKHOTSK 3 is at 9:41AM. In other words, you should be aware of train schedule if you plan to stop along the way.
Abashiri to Utoro, 50minutes - 60minutes from Abashiri to Shireteko-shari, and bus from Shari to Utoro, the bus is not that frequent too, so be sure to check the schedule here (there was only 4 bus that I take note of, 8:40AM, 11:30AM,15:50PM, 17:50PM,)
http://www.sharibus.co.jp/ A few of the JR arrive 5-10minutes before the bus to Utoro departs, so be sure to check the schedule. Eg. JR Senmo from Abashiri arrive at Shari at 11:25AM, while Norokko arrive at 11:22AM.
Your round 1 seems a little better, but I would probably do Otaru - Niseko - Hakodate - Lake Toya - Noboribetsu - etc