WFLF moved to the Orlando market circa 1990 as WGTO, the orginal call letters. WGTO originally was licensed to Haines City circa 1955 but was re-licensed to Cypress Gardens circa 1958. The move to Orlando was decided on a few factors including the fact that 540 could not move any closer to Tampa due to potection of 570 WTKN (now WTBN).
According to the FCC rules regarding city of license changes, it's permissable under certain conditions. First and foremost an entity cannot remove a community's only primary licensed radio service. I. E., if WGTO had been the only primary licensed (translators and LPFM are secondary licensed broadcast services) radio station licensed to Cypress Gardens, a COL changed would not have been legally permissible without identifying a substitute channel to replace 540. However since Cypress Gardens had two primary licensed AM stations - WGTO-AM 540 and WYXY-AM 1360 - the FCC authorized the WGTO COL change since Cypress Gardens would still have at least one primary licensed radio service - WYXY-AM 1360.
Also, although technically possible, from a legal perspective, considering Orlando already had several AM and FM stations licensed to Orlando, the FCC would not have authroized taking a station from a small community such as Cypress Gardens and essentially giving it to Orlando which already had local radio service. Hence, Pine Hills was chosen as the new COL as that community's first local service. This made it possible for the licensee to cover Orlando with a primary signal while legally NOT becoming an Orlando radio station. It was, and still is, a Pine Hills radio station from a legal perspective.
From a technical viewpoint, the towers were moved to an area South of Clermont, later re-located to and diplexed onto the current WYGM-AM 740 tower site, also just South of Clermont and due West of Orlando. The fact that WGTO (now WFLF) is 50,000 watts and covers half the state during the day (inlcuding and especially Orlando) is a "bonus" for the licensee allowing the station licensee to take advantage of attracting Orlando radio advertising dollars. So long as 540 provides a city grade or primary signal over the COL - Pine Hills - any other coverage is perfectly legal so long as the station's signal does not cause interfernce to another station or stations.
WGTO, later WWZN, WQTM and now WYGM was moved to Maitland under Paxson Communications, not Clear Channel. It was already located at Maitland Center under the Paxson created cluster when CC bought the station in 1997 for $693 million when CC acquire the entire Paxson Communications radio division. In 1990 WGTO was located in a free standing custom built studio/office building in Ocoee on Marshall Farms Road before Paxson acquired the station and moved the studios to Maitland.