One Small Step: Board per Client or software release? Client access, Workflows, Permissions, Reporting and Dashboard creation will need be outlines. is there Data import and export to other systems?
Relevant Skills and Experience
I have implemented JIRA/Confluence at 3 other companies right now and use it for my own business.
Proposed Milestones
$50 USD - Initial set up
$50 USD - Workflows
$150 USD - Permissions
$100 USD - Kanban Boards
$100 USD - All Dashboards
$100 USD - Issue filters
$100 USD - Client access and notification
$150 USD - Bespoke manual and training
$100 USD - Issue Import and configration
$61 USD - Custom field configuration
$50 USD - Notification configuration
$50 USD - General review and understaning of your Business model
$50 USD - Project Plan
$51 USD - Company branding and customization
Critical Thiking: Crawl, Walk Run - Do not aim for the end goal, but start at a manageable level (Crawl). Modify and look to the next items (Walk). Integrate completely (Run)
The most important thing is to make sure that the company has its process outlined. Once this has been outlined, then you can look to configure JIRA. There will be changes made on both sides (Company and application), but the most important item will be the flow and the buy in from the users and any clients you may want to give access too.
One of the biggest failures is to jump in to fast.
Pitfalls of configuration: To have too many Issue types, screen types and workflow types to manage. you would want to have these centralised and configured so that all project flow the same.