At the JTA TOD workshop a few years ago, I advocated extending the skyway by the JEA site and then swinging it south towards San Marco. Pretty sure Lake, TUFSU, and others disagreed. Now that this site plan is ready and I've looked at the site and surrounding area, I'm changing my mind. As others have pointed out, the Kings Avenue station is a short walk and easy bike ride from Healthy Town. Extending the skyway probably doesn't open any dense development/TOD opportunities to the east/southeast. It looks like the large 9 acre COJ owned parcel to the south of the JEA site is wetlands, or at minimum in a flood zone. Pretty much everything else west of Bishop Kenny is single family. So this may be the last urban frontier east of Kings Avenue Station and north of 95 for the foreseeable future.
Given the lack of development options east/southeast of Healthy Town, I agree that taking the Skyway directly south along Hendricks or Kings is probably the best way to go if there is to be an extension.