Looking for some help - Deed Restriction Violations

I am building some software that could be used to manage an HOA. It's all web based, and I have the basics functional for the following:

- Creating and updating Residence information
- Basic accounting for residences (Debit/Credit, cash accounting for residences)
- Assessment management (can create debit transactions that are applied to every residence in the HOA)

Now I want to start building some features around deed restriction violations and management but I am having trouble getting started.

I think I understand the basic flow for a violation:

- Identification and Documentation of a violation
- Send out 1st notice
- Check back and either close the issue or escalate
...and if needed
- Send out second letter, certified
- Send out request for meeting with homeowner
- Notifications of fines
- Legal action notices

My question:

How do most HOA's determine that an issue is the "continuance" of an existing issue?
Do you send pictures of the problem with the first letter? Second? Is it required at all?
Does anyone use email to send notifications to homeowners?

Thanks for any feedback.