This paper considers the potential future wherein the General Aviation (GA) infrastructure of airports and aircraft becomes an integral part of the commercial aviation transportation network. Further, this paper discusses inherent individual and societal risks sourced in the very characteristic that makes the GA infrastructure attractive: accessibility and ubiquity. Air traffic controller furloughs, mergers, surface transportation congestion and infrastructure degradation are a few examples of system discontinuities that have led to increased travel time for short and medium air travel (200-500 miles). These, amongst other constraints, are drivers of various initiatives that seek to mitigate these delays via transfer of travel demand from larger towered airport infrastructure to the General Aviation infrastructure via development of aircraft, business plans, operation oversight processes. An example being the nascent air taxi industry coupled with the development of the Very Light Jet designed to operate on 3,000 ft runways. The development of High Volume Operations (HVO) capability in the GA infrastructure (specifically non-towered airports) will subsequently increase risks to communities situated in the vicinity of GA airports via increased potential for accidents. Modeling and understanding these inherent risks in is important if public safety and negative reaction to operational changes, particularly at community airports, is to be avoided; a negative public opinion that could forestall the development of HVO. Similarly, the potential for security threats (i.e. use of aircraft as a missile) from unsecured community airports are greater, but qualitatively less severe than TSA regulated commercial airports. With the potential of 4,000+ additional airports being added to the national commercial air transportation infrastructure, a risk-based allocation of security resources would need to be implemented for efficient allocation of scarce resources.