I am using a variation of this but not handwriting (using a handwriting font) - I'm also a developer by day so with a csv (or any kind of spreadsheet) I am pulling the name from the 'Name' column, if there's a first/last name I strip the last name and lead off with a 'Dear James' or whatever. I think look in the 'Address' column and use the corresponding address, example: row 1 will have ['Name':'James', 'Address':'555 main street'] followed by row 2 etc. etc. followed by the body of the message. So it looks kind of like:
"Dear [Name]
Blah blah blah your property at [Address] and I would like to....."
Call the spreadsheet from the script and it does everything I need it to do including sending it to the printer. Script did not take long to write and I'm not sending out a billion letters... the folding can take a little bit of time so thinking about going with postcards.
Does anyone use stamps.com? I hear advertising for it, would it be easier than peeling/sticking on stamps? It would be great if I could automate the stamp piece as well.
We just had our house on the market but my wife decided she didn't want to move right now, so we pulled it off and did the letters come rolling in. I got a good look at this process from the other side, dozens of investor and realtor letters asking to either buy or help us sell the place. They really were all a blur. Pretty much the same letter in "slightly" different packaging - it opened my eyes to it being a numbers game , at least on some level. Some handwritten, some typed, some with pictures of the family, some with candy... yes, candy. Very interesting indeed.