I think the strategy is great. I know a couple of people having great success marketing to probates. I recently started targeting them myself. I only mail white letters, and I mail once a month month. I do NOT contact the surviving spouse with a probate letter...that's over the proverbial line for me. It's a sensitive subject to begin with and I'm not willing to open that discussion with the surviving spouse. What I will do is send a generic yellow letter maybe a month or two down the road, with no mention of the probate situation.
As for automation, I'm just doing it in-house. Since I only recently started, my list is relatively small compared to the usual mailing list of say 1000 leads you might pull from ListSource. I manage my leads in an excel spreadsheet and it's pretty easy to handle the monthly mailings. And I'll check the county records every so often and scrub the list manually to remove leads that may have already sold the property. Hope that helps.
You may want to get in touch with Sharon Vornholt. She's got a lot of experience marketing to probate leads and could give you a lot of good advice. You can find her here on BP or on her blog.
