In general, the historic downtown home has withstood the test of time. Depending on it's age, it has survived up and down markets, wartime, unemployment, stock market crashes, and the influx to and flight from the downtown area to the suburbs. Many builders will tell you that the wood used in older buildings is better than what we use now. Of course, some of the newer homes being built today have energy saving features that were not available 100 years ago.
Ask a local realtor to help you evaluate the two properties. There is value in an established neighborhood. There may be value in an up and coming neighborhood. Also consider commute time to work, gas prices, public transportation, and convenience to your particular life.
New roof is good. How about the windows, the plumbing, the electric, mechanicals, and insulation? How is the foundation? Which is more popular with buyers in your area; older home with character in downtown location, or newer home in suburb? Does the master plan for your city have anything to make the suburban home more appealing in the future?