Just remember that there are three fundamental steps here 1) Georeference the jpg so your GIS knows where it is in space, 2) Create a new dataset from the jpg in vector format, 3) Use the attribute table from your new dataset to conduct your analysis. I'm sure it sounds complicated if you've never done it before but it's really pretty easy once you get your head around the concept. You'll probably have to assign some attribute data such as "Damaged" or "County Name" to the polygons you draw but that is a whole other issue. Then it's just a matter of either editing your existing shapefile or creating a new one using the jpg map as a background. If something goes crazy and the map gets really distorted you can either start over entirely or delete the last control point you added using the 'View Link table' button on the georeferencing toolbar. You'll never get it 100 percent accurate, but you can get pretty close if you try. Repeat the process a few times and try to get the jpg as closely matched to the shapefile as possible.Now you are going to repeat the last two steps using a second point on the jpg map, preferably one that is relatively far from the first one, but just go with what you can for now.It may be very small, or it might be huge, don't worry, you'll fix that with the next step. You should see your map appear in the vicinity of where you clicked. Click on the corresponding point in the shapefile.Then click on the 'Previous Extent' arrow on the toolbar to zoom back to your shapefile and move the map so that you can see the point you picked in the previous step in the shapefile.I recommend finding places that are easy to identify such as intersections of major roads, sharp corners in boundaries, etc Find a point on the map that you can match to the shapefile you loaded in step 2 and click on it.Click on the 'Add Control Points' button on the georeferencing toolbar.In the Table of Contents, right click on the map and select 'Zoom to Layer'.Load the jpg of the map you want to georeference.Load an existing, vector shapefile of the counties you are interested in.Here are the steps I recommend following: Then you will use the 'Add control points' tool (first button after right of the combo box) to tell arcgis what points on the image correspond to points on a second data source that already has a spatial reference. To turn it on you just right-click on a toolbar, look for Georeferencing and turn it on. In ArcGIS this is done via the Georeferencing Toolbar, which is turned off by default.