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Chase has the infamous 5/24 rule, which states that if you have at least 5 approvals for personal credit cards through any issuer within the past 24 months (not just Chase) you will very likely be denied for a new personal card with Chase. Business credit cards do not fall under this rule.
Therefore, it makes sense to apply for any Chase cards early on, as you will likely be locked out from Chase if you have several successful applications in the past 2 years. The only exception would be the Capital One Venture X, as Capital One is known for rejecting applicants with several new cards – even those with a high credit score (including 800+).
Due to this, I took advantage of an elevated 90k miles SUB and applied for the Venture X as my 2nd slot in 5/24 in September 2023 (the Chase Freedom Unlimited was my first card in July 2023) and was approved! The Venture X has a $300 annual travel credit (via their portal) and a 10k miles anniversary bonus, which fully offsets the $395 annual fee and makes the card essentially free. (Technically better than free, as the miles are worth $185 per TPG’s valuation, meaning Capital One is paying you $80 yearly just to hold tge card!)
I plan on applying for 3 more Chase cards to finish my 5/24 slots, starting with the Chase Sapphire Preferred/Reserve in November/December 2023, then moving onto a hotel card a few months later (likely the IHG Premier), and finally ending with the Chase Freedom Flex.
Besides that, the more premium American Express cards (especially the Platinum & Gold) are lifestyle-oriented cards, and get most of their value through memberships and credits with partners (i.e. Saks Fifth Avenue, Uber, GrubHub, partner restaurants). If you can take advantage of the credits, you can offset most, if not all, of their annual fees.
For instance, the Amex Gold Card had a $250 annual fee, but includes $120 in yearly Uber credits and $120 in yearly credits for participating chain restaurants & delivery services (i.e. Cheesecake Factory, Shake Shack, GrubHub). If you can use all of those credits, your effective annual fee is reduced to just $10, making the card nearly free.
However, I prefer Lyft as a rideshare service, use the Divvy bike-share system in Chicago, and avoid chain restaurants, preferring to support local businesses. Therefore, I would get more value out of a card like the Chase Sapphire Reserve, which has an automatic $300 travel credit and a Lyft Pink membership (normally $199, includes 5% off Lyft rides and free Lyft bikes [including Divvy, CitiBike, etc.]) to mostly offset the $550 annual fee, effectively bringing it down to $51 on my end. Compare that to the Amex Gold, which would still have a $250 annual fee (since I am not interested in their partner credits), and the CSR is a better fit for my needs. As the saying goes “your mileage may vary”.
I hope all that information helps!