I'm ready to start a new game since I finally finished the MQ. I'd like to RP as a merchant who will work closely with the Khajiit caravans, opening trade routes between major cities and settlements.

In my previous games, I've always headed to Riverwood, but this time, I'd like to avoid the MQ completely, so I plan on jumping the road and head directly to Whiterun.

Can I enter Whiterun despite not having info about dragons?

If I return to Riverwood later, will I be constantly accosted to "tell the Jarl" or does the character stay by the mill with his sister until I react (or does he hang on the road, waiting for me to catch up)?

Any other helpful tips on avoiding the MQ completely will be greatly appreciated.

Thanks.