He resided in the Orlando, Florida area and was noted for founding and directing numerous youth orchestras and music programs throughout the region.

Jonathan received his master's degree at Colorado State University in Fort Collins, where he and Maureen would begin a lifelong pursuit of teaching music that would take them across the country.

"[4] Not content with assuming the role of a weak musical director, May would form a competing orchestra with former FSYO board members and supporters.

[4] Though this period marked a fractious time for the youth orchestra movement in Central Florida, with some patrons claiming there were not enough students, venues, or funding to support another youth orchestra in the Orlando area, May remained undaunted and would answer these concerns with his familiar humor and a prophetic movie quote: "If you build it, they will come."

May's leadership helped oversee its growth into five separate orchestras composed of about 200 students (ages 6–22) from several Central Florida counties.

[6] In just a few years the orchestra would grow to five groups and increasingly become known for its inclusiveness, as no student was denied the opportunity to learn music, as well as May's relentless efforts to raise awareness about the value of an orchestral education to children of the Central Florida community.

[7] As dedicated member of the Central Florida community, May devoted a great deal of his time bringing music to those that might not otherwise have the opportunity.

May served as Artistic Director of the after-school music-education program, which was available free of charge to all Flagler County public, private and home-schooled students.

Under his guidance, and as part of his desire to provide students with the most comprehensive orchestra experience, May's orchestras often performed with professional guest soloists and in venues across the globe, including in Australia, England, Scotland, throughout Austria, in major Italian venues in Milan, Fiesole, and at the Academy of Music at Santa Cecelia.

Always conscious of the difficulties of funding the arts but never doubting the need to do so, May and his orchestras sought to raise money for their trip by doing what they did best and holding performances for the community, as he told the press: "Selling cookies is not what we do.

[17] In the often-political world of youth orchestras, he retained an insouciance and positive attitude that allowed him to focus on the music education of his students over politics or status.

Upon completion of the emotional piece, OPO conductor Christopher Wilkins embraced Maureen May, who plays cello in the orchestra.

The piece, Tall and Small, was named to reflect the wide impact May's passion for music had on children and adults alike.

[23] The Make Music-Make History competition continued through April 1, 2011 with live audition recordings conducted by the Metropolitan Area Youth Symphony in March.

[24][25] The sold-out concert began with "The Tall and the Small," a 12-minute piece that the Orlando Sentinel reviewed as "reminiscent of that moment when the sun emerges after a long stretch of rain.

[9] In 2010, May was named as honorary founder of the Metropolitan Area Youth Symphony (MAYS) in the Orlando area, founded by his wife, Maureen, and longtime friend, colleague, and fellow conductor, Michael Miller of The Geneva School in Winter Park, with his daughter Emily serving as program organizer.