I have been investing for a while, but am looking to expand into probates.  I have opinions on what I may do and questions about your opinions.

These questions revolve around mailers.  I was going to:

(1) Send a professional white letter to begin with then

(2) send a postcard at 3, 6, 9, 12 months.  Additionally, I'd follow up with a call at each mailer a week later.

My list you ask?  To attempt to have better leads and keep marketing costs down (I'm already budgeting 1-2 grand a month), I will mail owners/heirs who don't live at the property in question.  I am not planning to mail the subject property.  I'm not planning to mail the spouses/residents of the actual property - only off premises heirs/executors

I get my leads daily.  Its not a monthly batch.  Ill likely just aggregate everything into a weekly mailer

Questions:

(1) what do you think of this strategy and

(2) What do you think about contact the live in/spouse vs only offsite heirs

(3) How do I automate this?  Id prefer not to code it myself.  Id like to take my march 1 lead and have it automatically add it to my June 1 list Sept 1 list, etc along with the leads for those days.  That way I just barf out one set of labels for that day, 3 months prior, 6 months prior, etc or whatever and slap them on the pile for that day ad drop them in the weekly batch bucket.  SAme with the phone numbers.  Id liek a dialy call list

(4) Last, how do I maintain this list and take out the trash/sold/mad people, etc?

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.

Just dropping my two cents. My wife and I have started a trial of a website called REIPro that allows imports of leads into their mailing system. It also can auto-generate the letters. It does however not have the rest automated. We have also looked into FreshSales which has much more automation of tasks, lead imports but does not fill in the forms for you. I would be interested in a more complete package if someone out there has opinions on this sort of thing. 

@Ro Carter and @Account Closed I use Excel as well and mail merge all my leads. Everything is done in house and I haven’t found any reason to pursue a more sophisticated system. I print, sign, fold, stuff, and hand address about 600 letters/month. The best purchase I’ve made is a $200 letter folder. Overall it’s not that difficult. I enjoy it. Try to be very consistent. 

As far as mailing cycles go, I really think it depends on your state law. In my area there is no minimum time limit put on property inside of the estate. The filing of probate and judgement of possession can happen in about two weeks, therefore heirs have the ability to sell pretty quickly. So I load up my mail on the front end. I mail the day after probate is filed, then 2 weeks, 2 weeks again, then put them on 45 day cycle. That’s what I’ve found works for me and my area. 

@Ro Carter Id like to throw in my thoughts on the automation portion of your question. I have been looking into CRM services they help you import lists, track leads and their stages, scrub lists. Here is a biggerpockets article to get you started if you have not looked into that system yet. https://www.biggerpockets.com/renewsblog/2014/02/15/using-free-crm-manage-real-estate-business/