I re-shingled the roof.

Most homeowners think the wood is included with roof installs but more often than not, contractors just replace the shingles and maybe a sheet here and there so it looks like the wood was replaced.  

Example: "Hey Insurance Company, I need to make a claim on my roof - there was a storm last week that did damage to the shingles and now I need a new roof."

An asphalt shingled roof can be easily stripped above the damaged ceiling area however the water could be getting under the shingles up-roof from where it's shown-up inside.

Work for a broker until you can hang out your own shingle.  

One of my buildings in lakewood has wood shingle siding and it looks like a pig with lipstick.

Some of the quotes I got from contractors have an insulation board that is put down over the existing wood style shingle siding, then have the new siding go over top.

I have lots of leftover shingles kicking around, nice in color.

You could even go the extra effort and send them pictures of the houses tall grass or missing shingles and the owner may not even know they are in such bad shape that they may be more interesting in selling quickly. 

I am a big fan of computerized applications but Ive seen plenty of people use that paper system.