I'm a young investor with big ambitions and ideas about getting into rentals.

You should connect with @Fed Finjap; I just saw on another post that he is also buying in the Chicago neighborhood ofLakeview and he recently went through some lessons learned on a 3 flat in Chicago.Check out his post:  https://www.biggerpockets.com/forums/922/topics/1223655-refl...

I'm struggling with the idea that it is somewhat normal in this market but it does seem like it would be a negative to potential tenants.

Should give you an idea as to whether it's worth it or not.  

JV, GP-LP so you leverage other peoples creditsThere are a few other ideas.

That said, we have traveled a lot and stayed in wonderful Airbnbs over the years and have always dreamed of creating an incredible experience for someone visiting Minnesota with a short-term rental as well, so we are definitely open to that idea and have some great experience as to what we know would provide an exceptional short-term rental experience. 

Alternatively, your sibling might use a 1031 exchange to defer taxes by reinvesting in like-kind properties, though this doesn't directly fund a primary residence.Other ideas include leveraging a HELOC on the rental properties for the down payment, taking out a 401(k) loan, structuring an owner-financed agreement, or a lease-to-own arrangement.

Additionally, when underwriting deals, you need to account for the general idea that repairs and maintenance will be a larger percentage of your rent, the lower your rental is.  

Any other ideas for how to solve this problem?

And yes they pay 60% of your Mortgage.Open to share ideas any time we have a free network to meet like-minded investors in Miami.Luis Maqueira