I would strongly suggest looking into Indiana as a place to own - since you are from here & the rest of the planet loves our back yard to invest in.- it's always good to see another Hoosier utilizing this great site!

To the extend that landscaping matters, I get around it by arranging the timing so most of my houses sell in the winter when everyone's yard looks about the same as mine. 

I spend so much time at salvage shops, finding such great deals on building supplies and have no where to put them!

I am assuming since it's a multi family, the owner would be responsible for the maintenance of the yard/snow & common areas (hallways/staircase).

Start in your own back yard.

The lot is completely flat as is the surrounding area, and the yard in general is saturated (not uncommon at this time of year).My initial reaction is that I should fix the gutters and get them draining away from the foundation, let things dry out and then evaluate the situation further next rainy season.  

The tenants are more longterm and in my experience consequently care more about the property / yard because it's almost like 'their' home as opposed to transitory students who generally view most everything as the landlord's responsibility. 

Given your situation and the answers to questions like these, maybe it makes sense to buy a 3/2 in a nice neighborhood with a yard and get a couple of roommates.

I rushed over and was able to salvage items out of the attached garage.

You could keep your yard green and it cost you $0.00