Have you looked into ArcScan tutorial ? Here is the link to it http://help.arcgis.com/en/arcgisdesktop/10.0/pdf/arcscan-tutorial.pdf .
I have done that in the past however, if you are planning a lot of image then it is a little bit too much. I have had never use WinTopo. You need to google it and compare for yourself to decide which one is best. Will you be able to use the image once you are done with the WinTopo work and then bring back it to ArcMap ? What is the result for that image ? This is something you need to think about it.
My question to you is why are you planning to use ArcScan ? what is your purpose to use it ?