There's another game that's been sending me a reminding mail every month. Perhaps you could implement something similar to deal with inactivity.
"Subject: ... - Are you bored? Come back to ....
Hey ...,
We read your eulogy in the streets a while back. You caught a tough break, kid. But you should know that since everyone thinks you're dead, this gives you an advantage...
Everyone deserves a second chance. A chance to rise through the mafia ranks and make something of themselves. A chance to show those other goons that you have what it takes to run your own crew... or even your own city.
You want an incentive? We can respect that. Since you showed so much promise, how about we throw in 7 days of the ... for free? Yeah, you heard right. We'll give you 7 days of the ... to help you get back on your feet. Just don't go spreading that around - we have an image to maintain, you know.
Now, it's time to go show those bastards at ... just how dead you are. Good luck, kid.
Sincerely,
..."