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Just ended 2L at a CCN, probably around top 1/3 of the class, LR. Summering at a "V5" firm for the summer, looking at district clerkships atm. Have LOR lined up (TA'ed for several professors, one of whom has explicitly stated that they will go to bat for me). Grades are fine, but unfortunately, I missed the opportunity to boost them as a 2L, as I was a little burnt out from the summer (recruiting ended in mid-August for me). For context, I'm open to clerkships across the country, though the East Coast would be preferable, and am politically flexible (barring extreme right- or left-wing outliers).

Now that I'm starting to realize how difficult applications are, I've been debating putting off applications for a cycle or two - not because I'm afraid of striking out, but because I only have limited opportunities to utilize my professor's connections (the professor said to send them a couple of judges I'm interested in, and that they would put in a word for me). Put another way, I'd love any advice on the pros and cons between 1) applying this cycle w/ a "less competitive" application and 2) delaying the application a year or two to prepare a more "competitive" application. Any advice on non-legal considerations (Cost of living, adjusting to non-firm life, etc.) would also be greatly appreciated as well!

It's probably not true that you in fact have only limited opportunities to utilize your professor's connections. You could apply both now and then later and use your professor's connections in both instances. The professor probably didn't mean "you have one cycle in which I will be willing to make calls to go to bat for you; if you strike out in that cycle then I will not be helping you again." If you'll just feel better and more confident waiting until you pull your grades up (which I totally understand), then that's another thing.

I agree that unless your prof has said something to the contrary (which would be unusual), you don't really have limited opportunities to benefit from your prof's connections. In which case, why not just try now and see what happens? I don't think applications are that difficult, in the sense of taking up so much time.

Also, what are your goals? How much more "competitive" do you need to be for what you want to accomplish? People argue ad nauseam here about "ranking" clerkships but that gets kind of silly quickly and doesn't mean too much in a vacuum. If by East Coast you mean NYC, those clerkships are particularly tough just b/c of the number of people who want to be in NYC, and I have the impression that SDNY judges at least prefer work experience anyway (not sure about EDNY), so yeah, you may have a better shot there a couple of cycles from now. But depending on what you want out of clerking, you don't have to do SDNY/EDNY to reach your goals.

On a personal level, it can be easier to clerk first and then go to your firm job and settle in, rather than risk working for a year or two and then moving (maybe across the country) and moving back again when your clerkship ends. Some people prefer not taking a pay cut so would rather clerk before moving to their firm, some people prefer to work for a year or two and save some money for when they do have to take a pay cut. There are pros and cons for both.

Just keep in touch with your professor, they'll help you out whenever. As long as you keep in touch.