Jim,
I don't think it is a crazy idea to self manage the property until you get a few more properties but here are some things to consider with a property that is an hour away.
1) Condition of property - if the building is older you may possibly have more maintenance to consider versus something that is newer.
2) When there are minor maintenance calls, I often have a handyman to go over while tenants are home and fix the issue, I confirm with the tenants that everything is okay, and pay the handyman. There is no need for me to drive there. However, if the maintenance issue is an bigger one, I usually need to make several trips: Check it out myself first, meet someone to get an estimate, check progress of work if it is over multiple days, review final work, etc. prior to paying for the services. This can add up very quickly especially in Chicago where traffic can be a pain.
If there is a handyman you trust, you can sometimes just work with them so they can be available to you when needed (this may lesson the amount of trips you need to make if you can trust them).
3) Tenants - Based on prior experience with tenant, do the often report maintenance issues or minor things all the time? When I do tenant screening, I often ask about this to their previous landlords.
There are obvously more things, but hope this helps. Keep in mind, I would log your trips so that you can expense the mileage for your trips as a business expense.