Well first of all @Joshua Martin, I have to say I wish we had prices here in Alaska like those you've mentioned! Currently, I don't think you can touch a decent duplex for less than $200k or close to that and 4 units are $400k to $600k depending on area and condition, of course.
IMHO you need to consider, your age, your strength, your "taking care of all the little problems" abilities, the distance from where you live (if you don't owner occupy) and then think forward a few years and imagine that you've fixed and fixed and fixed a "beater" property that has been very difficult to keep rented because the area is awful and real estate HAS NOT gone up in value. You'll have tax write-offs and hopefully some cash flow, even after your fixing, but think about how much nuisance it is...and is it worth it? Maybe it is!
Now think about the property in the great area that is easy to rent, doesn't need much work, and in general you can sleep at night and not worry about it. If real estate HAS NOT gone up in value you still have a property in a desirable area and have less/little trouble renting it.
I can't even imagine living in a huge city like Milwaukee, but you will have lots of area choices. If you are going to be the manager, then try really hard to "like" the areas closer to you because you'll get really sick of driving clear across town to let someone in who lost/forgot/locked in their keys or fixing the toilet. Again, all this if you decide not to owner occupy.
After all is said and done, look at the worst case scenario, within reason, make some intelligent calculations and decide if you can still pay for and repair and love your investment.
Joshua, look for a motivated seller, one who will carry the note for you, be patient and buy what you can really handle.
blessings,
