1. Compare D8 and D7 performance
2. Improve site functionality
2.1. Improve admin UI and site flexibility
2.1.1. Modules
2.1.1.1. Bricks
2.1.1.2. Panelizer
2.1.1.3. Paragraphs
2.1.1.4. Panels + Layouts
2.1.2. Distros
2.1.2.1. Panopoly
2.1.2.2. Lightning
2.1.2.3. Thunder
2.1.2.4. Spark
2.1.3. Research alternative systems
2.1.3.1. Squarespace
2.1.3.2. Wix
2.2. Improve CK Editor and media embedding
2.3. Content management, sharing and syndication
2.3.1. Deploy
2.3.1.1. Idea: ability to see site where all the content is shown as ready to be deployed or drafts
2.4. Better sliders and page banners
2.5. Accessibility
3. Hire new developer
3.1. Prepare requirements
4. Explore Drupal 8
4.1. Check google alerts about Drupal 8
4.2. Read case studies
4.3. Talk to developers
4.3.1. Drupalcon
4.3.2. EduDU
4.3.3. FFW
4.3.3.1. http://www.ymcamn.org/
4.3.4. Fabian France
4.3.4.1. Integrated paragraphs and panels in custom project
4.4. Watch Drupal 8 videos
5. Architect new site
5.1. Write down current sites functionality and customizations
5.1.1. Map current site functionality to D8 modules
5.1.2. Architect custom modules
5.2. Check D8 modules status
5.2.1. http://d8status.md-systems.ch/
5.2.2. https://contribkanban.com/board/contrib_tracker
5.2.3. Map D7 modules to D8 ones
6. Evaluate Drupal 8
6.1. Evaluate core differences from D7
6.2. Evaluate modules
7. Create a Brief
8. Create prototypes and talk to users
9. Evaluate risks
9.1. Evaluate performance
9.1.1. Investigate caching strategies for D8
9.1.1.1. Bigpipe module