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You must use your Downtime to make a Day Job roll, so yes.
After each adventure that grants XP, you gain a period of Downtime before your next mission. During Downtime, you can attempt a trained Craft, Perform, or Profession check to see how much extra money you earn—this is called a Day Job check. At the end of each adventure in the Roleplaying Guild, you have the opportunity to make one Day Job check.
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There are additional ways to spend Downtime, many of which are performed in place of a Day Job check. These may include special boons that are earned during an adventure.
Venture-Captain, Germany—Hamburg
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Also, can I use inspiration on a day job roll?
Last time I checked, the general consensus was that you can use it as long as you're allowed to roll the extra dice without spending inspiration points. That's also how I would rule it at my tables.
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Here's a link to when Andreas previously addressed the OP's question about using inspiration for day job rolls in a thread from 2013. I've been doing it with my Swash-igator using free inspiration on Knowledge(Local) by way of the Information Broker vanity from the Pathfinder Society Primer. I've had 2 GMs (including a VC) question it, but they've been satisfied with my reference to the thread below, and an explanation that it's an unlimited, always-on ability.