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I think I know the answer here, but I don't want to do anything to screw up my chances at OCI in the fall. I have an offer to work for a State Appeals Court judge who I think I would enjoy working for. He has two openings, one would be an 8 week internship starting after finals in May, which would give me about 6 weeks off afterward before Fall term starts. The other opening would be for a 4 week intership when he gets back from vacation the last 4 weeks before school starts.

The reason I want to take the 4 weeks is because it will give me a chance to work full-time up until that point (in non-legal work) which would be very big for me financially. In addition, I am still in the running for a couple of paid legal internships where I could do both if I take the 4 week assignment with the judge.

From what I have gleaned here, "prestige" is not very relevant and the important thing for OCI is simply to have done some legal work during 1L summer so you have something to talk about during the interviews. Will this put me at any disadvantage whatsoever in comparison with the majority of my peers who will be working 8 or 10 week internships this summer? Would I even have to disclose that it was 4 weeks? Obviously, I would disclose if asked, but I don't know if that would even come up.

Do the 8 weeks

You'll have a 1-2 week learning curve and if you only do 4 weeks you will have very little substantive work to talk about at OCI. The interviewer will want to talk about substantive cases you've worked on and will grill you on aspects of it to assess, among other things, 1. your ability to articulate them intelligibly and 2. your enthusiasm for practicing law. You want to maximize the above two aspects by getting as much interesting substantive work as possible.

The only people who say the length of your internship doesn't matter are the ones with short internships.