Models of searchable resources adaptable to Legacy Winchester:
https://americanarchive.org/ - Indexing American History. Comprehensive.
https://oldfilm.org/collection/index.php - Extensive indexing of motion picture (film) and video.
Boston area Newspaper Archives https://newspaperarchive.com/us/massachusetts/boston/
Winchester Town Archives http://winchester.pastperfectonline.com/
The Internet Archive, IA, ( https://archive.org ) allows uploading but is not easily searchable.
American Archive of Public Broadcasting http://americanarchive.org/, a collaboration between Library of Congress & WGBH Media Library & Archives
Indexing/Search Front End Examples
The Library has pointers to resources in the Local History Room and http://www.winpublib.org/reference-and-research/local-history/local-history-overview
The Internet Archive, IA, ( https://archive.org ) The Winchester Library uses IA as its high level index of sorts for the Winchester Star and the Winchester High School yearbooks. The index is held at the library website.
Winchester Star from 1901 has been digitized at http://www.winpublib.org/elibrary/winchester-star
The Winchester High School yearbooks are also in IA http://www.winpublib.org/elibrary/yearbooks
http://fixitplus.americanarchive.org/ Editing speech-to-text transcripts.
https://www.technologyreview.com/s/409091/searching-video-lectures/ (c2007) Browser that converts audio to text and searches.
Library Management Software
Mass Memories Roadshow http://openarchives.umb.edu/cdm/landingpage/collection/p15774coll6 / uses Contentdm https://www.oclc.org/en/contentdm.html
Tools for search/information/data presentation:
Timeline (free and paid) tools to try out: https://www.ispringsolutions.com/blog/top-10-free-and-paid-interactive-timeline-makers/
Sutori is one of the free "timeline" apps. https://www.sutori.com/