Yes that is why it says when you Research at a location that gives a bonus on the subject you get to make the check as if trained. Your free rolls are normal at first and will give you a reason to explore the town/ask questions.
No they had a max DC allowed that you could find out through Gather Info. Only so much the locals know or are willing to reveal. So you would still need to research to find out the rest.
What places are available to 'research' history in this town? I only see mention of a library. Can we assume anything else? Museum? Time Capsule we can dig up?