Is it redundant/hard to get an MBA after Wharton undergrad?

You're pretty young. Have you asked yourself why you want an MBA? Not trying to dissuade you form pursuing one as I will probably get one myself in a few years. Think it through thoroughly. Make sure that it lines up with your career goals. There is no point in going to school and loading yourself up with debt if you don't need to. Also think about the opportunity cost of not working for those years you're in school. The numbers start to add up quickly. I don't think top MBA programs would give you shit for working on the street. They take plenty of people who work on the street and I don't think it makes you look like a money grubbing person as you stated. Just make sure that you have a cohesive story as to why you're doing what you're doing and why you want to go to business school. It might not be 'dumb' to pursue an MBA out of Wharton, but I might ask you why? Other programs are just as good with job placements. Wouldn't you rather live somewhere new for a few years and build up your network in other places? Just something to think about.

I think you would be in ridiculously good company if you went Wharton - Wall Street - HBS (or the like). Look at the upper management of large financial institutions, you'll find a swath of people with that exact career path.

All else being equal in the schools (location, experience, price, etc.) I'd say that Wharton provides greater downside protection from a purely a finance prospective. Things change and you may not in fact want to get an MBA / need to get an MBA. Wharton will provide a superior undergrad education for finance so choose that because it makes the most sense now.

Unless you're gunning for the top buyside gigs out of undergrad, Columbia will do you just fine from the perspective of recruiting. If you are smart, motivated, and go to a target, getting a job in IB isn't too difficult. You definitely have to work for it, but coming from Columbia won't put you at a material disadvantage for most opportunities.

UPenn and Columbia are very different schools, and you should pick the one you feel is the better fit. Unless you already have your mind set on a PE / HF job (and if you're interested in PE, I would recommend the IB route first anyway) at one of the top funds out of undergrad, I wouldn't focus too much on the job aspect with regards to this decision.

First question: No, MBA programs would not hold it against you for attending Wharton and working on the Street. In fact, pre-MBA finance related jobs (Consulting, Financial Services and VC/PE) comprise ~45% of the incoming class at HBS. One could argue that attending a school like Wharton (or Columbia for that matter) would give you a better chance of landing one of these jobs, which would in effect increase the probability of you being a more competitive applicant when considering your MBA (note, I am not saying you need to do finance to go to a top MBA program).

Second question: I have many friends who did Wharton undergrad and then the typical IB to PE route. A majority of those friends will be getting their MBA soon given the nature of 2-3 years and out at a majority of PE shops and many of them are considering Wharton MBA. In general, they would argue that receiving an MBA is somewhat redundant in terms of content they will learn given their undergrad experience, but they also cite that it's important for a) networking opportunities and b) job flexibility with respect to a change in career and/or rise within PE. As some have previously said, Wharton undergrad to Wharton MBA is not uncommon and wouldn't be considered a dumb move if you were getting your MBA for the right reasons.

You'd be completely fine at both. If I had to pick between the two, and I knew I was planning on going back for an MBA, I'd probably go to Colombia just to have a more diverse experience. From the friends I have that went to Wharton undergrad, it's clearly a great program, but it's pretty intense as everyone is basically gunning for the same jobs. You'd also be learning many of the things you'd end up learning in B-School. Colombia will be a little more diverse and because Wharton is better than CBS for an MBA, in a few years when you're gunning for an MBA it would be nice to be able to end up at Wharton and have that be a different branding on your resume rather than Wharton Wharton.

As someone said above though, the biggest thing is to visit both and decide which school feels better. Both will get you to pretty much any career you could want out of undergrad so pick where you'll have the best experience.

Wharton is a better name, but remember you'll still need to Beast it (