Just do it. Generational movement coming to Delta. Plus 321NEOs on the way. Grab you a Captains spot and get comfortable. Plus you'll look good and get paid good commanding a 321 which is nearly the same size as a 757. Then when you have the seniority to go 330 it's a quick 13 day course.
Don't worry about little things like uBers and hotels. Just 3-4 days of GS(PLENTY of opportunity over the next few years in NYC) pays those tiny costs for a year+. With all the movement happening you'll be able to bounce out of NYC rather quickly unless you mess up and end up liking the base
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