Some areas to look into:
An 11x17 flatbed scanner can be pricey; if you have the volume, then it should be justifiable. Look at
or
websites for a start on what's available. There may be a 'service bureau' that can scan these larger images. They often have larger drawing capability. File sizes can get large and it may be possible for them to upload the images to your email account.
One of the problems you will encounter is 'matching' the various 11x17 scans.
Many municipalities (in our area) have autoCAD compatible 'mapping' information. This is available to 'scrounge' or purchase and will provide a base map. Lindsay, Ontario, for example, has this info available that can be purchased for ??/hectare. It shows streets, houses, walks, roads, hydro poles, water and sewer lines, etc. The CATV stuff can be added to this.
Your local planning office may have drawings available that can be scanned and vectorized to provide base plans to work on.
There are a few raster to vector conversion programs available. The ones I've encountered are a 'hit and miss' and very dependent on the quality of the scanned image. These will convert the scanned image into an autoCAD and then the various 11x17 vector drawings will have to be pieced together.
There are also some firms that do this. I've used one that is located about 60 miles from here to scan Hospital Plans for renovation work.
What you are proposing is becoming more and more common and is often referred to as a GIS.