Good questions, Matt! First – re: switching from the Preferred card, make sure you apply directly for the new one, not just call and request to switch cards otherwise you may not get the bonus!

Regarding keeping the card more than a year – because of the $300/year travel reimbursement, you’re really only looking at a $150/year annual fee. So the question you should ask yourself is, will I get $150 in value by keeping the card for a second year? There are a few scenarios where I think the answer here could be yes:

1) This card gives you 3x points on dining & travel. Many other cards only give you 2x points per dollar. So if you will spend at least $10,000 a year in dining/travel, that additional 1 point per dollar spent bonus will equal $150 or more available to you in the Ultimate Rewards portal.

2) If you’re a frequently international traveller, the Priority Pass benefit could be worth at least $150. I estimate lounge access is worth about $15 per person, per visit in free drinks. So if you’re travelling to places with a Priority Pass lounge at least 10x a year (or 5x a year if you travel with a guest), then that alone will equal the annual fee.

3) You may be able to get Chase to negotiate with you regarding the annual fee. If you call about a month before your annual fee is due, I’ve had luck working out statement credits and/or new bonus offers in order to keep a card open for another year. See this article for more on that: https://unintendeddomesticity.wordpress.com/2016/05/06/how-a-quick-phone-call-earned-me-12000-points/