Hello,
I'm planning some paint work on a high mileage car - my primary concern is to keep it cheap and mainly I just want it to look good from a distance.

My biggest problem is a chipping clearcoat.  The roof and trunk are probably going to be bare basecoat by spring.  I'm HOPING I can just remove any remaining clear, prep and re-clear those areas.  Is that feasible??

Also - what would be a decent economic sprayer?
And would a compressor like this:http://www.harborfreight.com/cpi/ctaf/Displayitem.taf?itemnumber=40400
be able to hold up to a sprayer?

You will have to sand and feather the clearcoat.  Once the clearcoat lifts, the underlying paint (and color) becomes damaged and must be primed and repainted. The compressor you list would work fine. I would look at Northern Tool and Equipment, something like: http://www.northerntool.com/webapp/wcs/stores/servlet/ProductDisplay?storeId=6970&productId=22130&R=22130 would work.

You can spend more money on a professional sprayer so it depends on how often you will be  spraying paint. Look at http://www.binks.com for more expensive sprayers.