First step I would checkout what jobs are available in your area or where you would like to relocate. Since you're familiar with web application development I

First step I would checkout what jobs are available in your area or where you would like to relocate. Since you're familiar with web application development I would consider learning Rails (Ruby) or Laravel (PHP) . . . look at the opportunities at weworkremotely.com and larajobs.com to get an idea of the requirements. Maybe touch base with local agencies and see if they are have any openings. The best way to expand your skills it to take on paying projects maybe from family, friends or associates initially and start building your network. Some other sources of inspiration are StartUpsForTheRestOfUs.com, Patio11, Nathan Barry and Brennan Dunn for opportunities to start your own SaaS/Product business if that's interesting to you. Enjoy your time off. Good luck with your career change.