But it seems like securing financing for this kind of deal would be fairly straightforward as long as my financial situation supports it.

Some will call you for everything Overall Section 8 is great as long as you screen the tenants the exact same way you would screen any other tenant.

The rental demand in OP has been very high for as long as I've been investing there. 

Help them with the app and getting set up as long as they have a smart phone and for me it hasn’t been so bad)

It’s a great option to get started as long as it meets the second home loan requirements.

Like the others before me have stated, self management is not at all complicated and in my personal opinion (everyone has one, some are different) is the better option so long as you have a good system in place.

As long as I sell and buy through the title company, they do everything. 

You will be fine and you will crush it as long as you don't graduate and go buy a brand new vehicle and take on other bad debt just cause you can.Note: This is all the advice I would give myself if I could go back 15+ years and talk to myself in college. 

But as long as I’m paying the rent to myself, it’s fine.Any advice on how to put this deal together and be fair to both sides?

You can rent by room, increasing the overall rent price of a house, and as long as you screen the same way you would for any tenants, you get respectful, quiet, hard-working tenants.