For the most part, Dish_in_the_sky's advice is excellent. I live in Salem and receive the Cleveland stations using a CM 4228, a Winegard YA-1713 high band VHF antenna and a CM 7777 preamplifier. I'm about 55 miles from the Cleveland transmitters.
Based on the TV Fool information, I'd guess that your actual location is on relatively low ground (1 edge and 2 edge at 40 miles from the Cleveland transmitters and 2 edge at about 30 miles from WNEO), which means you'll need a large outdoor antenna setup mounted as high as possible. You might also want to consider an Antennas Direct 91XG for UHF reception. It has a much lower wind load than the 4228. If I were to do my setup over, I'd use the 91XG instead of the 4228. You will also need to use a high band VHF antenna like the YA-1713. The 7777 has inputs for both a VHF and UHF antenna. I do not recommend a combination UHF/VHF for your location. I realize that your parents do not like the idea of an outdoor antenna, but they may not have a choice if they truly want to receive WOIO and WJW via an antenna. WKYC, channel 3 will broadcast its digital signal on channel 2 until 2/17/09 and will then move to channel 17 on that date. You probably will not receive channel 3 with the YA-1713/4228 or YA-1713/91XG setups until 2009. If your parents don't want to wait until 2009 for channel 3, you can use an antenna like the Winegard HD-4053P instead of the YA-1713.
WOIO, channel 19, is broadcasting its digital signal on channel 10 at very low power, 3.5 kW ERP. They will stay on channel 10 after the analog shutoff with no increase in power. On 2/17/09 WJW, channel 8, will move its digital broadcast from channel 31 to channel 8. WTRF, Wheeling and WTOV, Steubenville will be moving their digital broadcasts to channels 7 and 9 respectively in 2009. WTRF's transmitter is about 60 miles from Canton and will not be at full power until after the analog shutoff. There are some FM stations in the Canton area; so you'll want to make sure that the FM trap switch of the 7777 is in.
You'll need a rotator if you're interested in receiving more than the Cleveland and Akron stations. You will probably be able to receive at least two of the Youngstown stations (WKBN and WFMJ). Youngstown's WYTV will probably be a problem due to its low power and low transmitter antenna height.
With multiple long coax runs, you will probably need a distribution amplifier with multiple outputs placed between the 7777's power supply and the TVs. You'll then run a separate coax from the distribution amplifier to each TV. Make sure you use high quality quad shield coax.