Weather cools, people are busy with school, resting from summer, prepping for the holidays, etc.

I understand if that is all that is available in your school district.

We have been sharing a car since 2020 in different households when she worked from home and attended college online.She worked and studied, maintained good grades and was compensated for it via her school and the system.

Have you thought about targeting mid-term rentals, particularly given the med school proximity, or STR given the hotels nearby?

My name is Jewett Richardson, and I’m a recent college graduate with a degree in Construction Management.

That curriculum you are following was designed for you by the school this way. 

My main concern about actual house hacking for a few years in a row is that we don't want the kiddos to have to change schools once we relocate up there.I'm thinking about getting an appreciation-oriented duplex/triplex in a pricier market with good schools that we could stay in for several years, and saving for an actual cashflow property that'd we buy as an investment property instead of a house hack.

You even graduated from IU so you have access to some awesome loan programs from IUCreditUnion.Keep your job and connections to buy a house, then rent out rooms to traveling nurses. 

You want to consider the quality of tenants you get and being in a central area means people can get to their jobs / school conveniently.

It's so hard to say generally what problems might come up, but the first that comes to my mind is work history - do you have 6 months on the job and a 2 year work/school history?