If you are comfortable with business cards, I'd go right out the gate with an Amex Platinum biz or Gold biz for the the higher sign up bonus. On the Plat it's 150k for $15k in 3 months and there are annual credits which if used strategically can offset that first year AF of $695. The gold biz is 130k MRs for $10k spend in 3 months and the AF is $375. What is more compelling to me about this one is the $20 monthly statement credit at office supply stores. You can purchase gift cards like
Amazon, Delta or wherever you shop normally at an office supply store for $20 each month to offset the fee which would bring it down to $135. If gas and dining are your two most frequent spend categories each month you'd also get 4x for that. Then, at one year, I would downgrade the card to the Amex Blue Business Plus which is a no fee card that will keep your MRs alive and transferrable to airlines. It earns 2x on everything up to $50k spend per year. Some would say get the SUB for that one also rather than product change but the SUB isn't often that good. In any case, having one will leave you open to another Amex biz Plat or gold via the occasional upgrade offer. You can go a similar route with the consumer plat and gold cards but there is no downgrade path for a no fee card. You could get the SUB for the Everyday preferred card which is a $95 AF and has decent earnings for groceries at 3x and a 50% bonus on MRs earned when you make 30+ purchases per month. 130K MRs on the biz gold are worth $1690 as DL miles in our scenario above. The 150k MRs are worth $1950, an AF of $695 on year one and $95 on years 2-5 comes out to $1075 and you're still ahead on a consumer card with getting the everyday preferred card before you cancel the plat card. The 130K MRs on the biz gold are worth $1690 as DL miles in our scenario above. However, when you PC to a Blue Business Plus card after year one, the years 2-5 and on are $0 so your OOP cost for the card was only $375.