They may require you to get a new tenant before closing (have a signed lease and security deposit). 

I would consider putting a cheap wifi security cam inside the front door to get notified of motion. 

I put all of their names on 1 lease, though give them the option to pay their portion separately, always take 1.5 months security because college students love banging counter tops, throwing beer bottles, and tossing each other into walls after 2 shots of gin.Students typically get their refund check end Sept-ish, I give them an option to pay Fall semester Sept-Dec (4 months) and spring semester Jan- May (5 Months)  up front, with no discount. 

I secure the property and does the rehab, and he is paid on the back-end once its occupied and refinanced.How does a deal like this work?

As such, in an effort to satisfy my own curiosity, is it ridiculous for me to consider cross-collateralizing two vehicles to secure a loan and get started with a house-hackable duplex or other small investment property?

If your local market has a shortage of open apartments, people may be applying to multiple places even if they aren't sure they want it, in an attempt to secure housing.

I would also either have a realtor or yourself perform some bona fide comps. 

Contract is on a 4plex under performing and 3 out of 4 units are empty.

You can use a line of credit to perform a majority of the rehab and then pay it off once you refinance.

If you must resell at a 9.5% cap rate:                                                     Year 1              Year 2               Year 3           Year 4                Year 5IRR Before Tax                         -45.20%            -7.54%                6.68%          13.02%              16.17%"If you can resell at an 8.5% cap rate:                                                     Year 1              Year 2              Year 3            Year 4                Year 5IRR Before Tax                           3.09%              17.12%            20.84%          22.03%               22.33%How do I go about performing such an analysis?