In a hardened insurance market that's causing grief for pilots of complex and tailwheel models, Maryland-based SkyWatch Aviation Insurance has been gaining attention for its modern approach to assessing risk. Using AI models to better match a pilot to a policy, the company has a website utility where pilots enter their information and the program shops for coverage with a variety of underwriters, and buyers can often score coverage on the spot. SkyWatch is credited for working with AOPA to create a senior pilot insurance program to help aging pilots get liability insurance in hopes of stretching their flying careers. To learn more about the company and for an update on the current market (and for tips on aircraft upgrade decisions with insurance in mind), we talked with SkyWatch's senior underwriting manager, Alon Admi.