Just realized after typing this all up, that you stated:
(using OS Maverick)
If you have a Windows XP or later computer available to run as a email creation server off to the side, the info below applies as a method to pull this off. The Mac computer can then open the e-mails created from the Windows computer just as you open other e-mails from people who send you e-mail from Windows or Linux systems etc.
This would be so much easier if you made a website to visit when in need of looking at this info. As far as what I am reading you want to spam yourself with this info on a rotation if I read this correctly. While this can be done, its far more involved than a simple website with a java script that reads in the day or uses a random generator for content to display and applies a picture etc to the web page etc.
For this to work via e-mail for FREE you would need to do some programming because I dont know of any other way around this as for I dont believe you will find a software on the market that is an install and leave computer running to e-mail you to another computer etc.
Do you have any programming experience and if so what languages and to what level?
Best Option below for Windows computer e-mail creation only:The most simplest method I can come up with would cost you about $69 by use of this software here:
http://www.jitbit.com/macro-recorder/purchase/Basically you would have to have a computer running 24/7 just for this purpose of sending yourself e-mail. You then create a macro that constructs the content you want to be included in the e-mail running through all the motions of what would normally be necessary to send an e-mail with attachments etc, and send it to yourself. Then end the macro recording and compile this to an EXE. Then save this EXE such as Monday.EXE, and then create other macros that e-mail with attachments for the other days of the week etc, and save them here in this same folder. So you now have 7 EXE's Then you create 7 individual scheduled tasks to windows scheduled tasks to trigger to run the EXE of this macro at say 1am. At 1am the schedule task runs and with you maybe sleeping your computer comes to life with mouse pointer moving on its own and logging in to your e-mail and doing everything that you originally did, and then sending the e-mail. Then when you open your e-mail later that day you have an e-mail to yourself to open.
Now you probably would want to not have every day of the week predictable. And to do this you would want to randomlze it. So you could if you know how to program start a random e-mail lottery program that picks out a random e-mail to send and so you can rename the e-mail macros that are 7 days of the week to 1.exe, 2.exe, 3.exe, and so on for as many different ones you want. So say you have a pool of 10 different e-mail makers now and the random number from 1 to 10 is 4, it will run the 4th one at 1am, and then the next day its 6, and then the next day its 1, and then the next day 9, and so on and unpredictable.
I really like this macro recorder because its very very handy for making something happen that would otherwise be complex and many programming hours to pull off a far easier task to pull off in little time with some creativity for redundant tasks.
Here is the software that is pretty easy to use. You need to have the Pro version for $69 in order to make EXE's, and you would need to have a 2nd computer that runs 24/7 that sends the e-mails out or if run on this computer if its a laptop that you take around with you, your computer would have to be on to send the e-mail to itself at say 1am etc.
http://www.jitbit.com/macro-recorder/
