Hi Silly...
I am biased since I live just south of Covington... I think it's a nice town. Yes it has problems (crime, drugs, blight etc). But there is a little thriving downtown on a river front you can live in the "hood" of Covington (I don't mean the bad areas but you always run some risk in the city) and be safe.
If you have a walking buddy.. I'd definately walk around Main Strasse at night and drink (bar hop and eat).. I feel very safe even by my self in those areas.
You can still pick up an old house for a decent amount in these areas. They are also redeveloping a lot of areas into townhomes and loft style living for those that want to be connected to the city.
Cross a bridge and your in OH/ Cincy (a quick bike ride or walk) to downtown Cincy.
I've lived in Park Hills (at the top of the big "cut in the hill"), Covington and now Villa Hills. Villa is more burbs with people that go with kids. However my best friend lives in a 2 bedroom in a semi safe area (safe enough my kid is safe to play in their yard and street but I wouldn't want them walking around past dark in certain directions). Their 2 bedroom is adorable and about 55k.
Hope that makes sense.
http://www.nkyvillage.com/
http://www.nkyvillage.com/things_to_do.htm
I've been to most of these places and being a 30 something with kids.. I still get out with the hubby to hang out when I can get a babysitter.
We have a great Octoberfest and Maifest (parties where you can drink outside!!).
Other areas to consider --
http://www.newportonthelevee.com/
http://www.cityofparkhills.net/
http://www.city-data.com/city/Park-Hills-Kentucky.html
http://www.realitytuescafe.com/ (the best little coffee shop!)
http://www.newportky.gov/index1.php?res=1024
Good luck!
We also go to Newport on the Levee (one town over)