These are wild guesses on some spots he may have headed towards: Since I'm utterly ignorant of the area, sea fishing, what the possibilities are, it would take input from locals to give all this the once over to think through what would have been feasible for him, least noticed, near or far, weather, conditions, being seen, etc... Most places keep their security footage for a month, the sooner the public in Lynn and Salem and beyond know to check, the better.
Going on the idea that these types of people may be driven to comfort zones where they are active. This RSO worked in sanitation and commercial fishing, and judging by where Jaimee's phone and other items were found on Technology Way, a fairly industrial type area, then the last point just kind of looked like the background in his facebook page, on the beach. This is a bird's eye map from 2012 while the aerial maps are from 2014.
http://www.bing.com/maps/?v=2&cp=r2jmw692r8cj&lvl=14&sty=b&rtp=



.42.484942_-70.932036_near%2020%20Spring%20Rd%2C%20Lynn%2C%20MA%2001902___a_~



.42.495089_-70.924489_near%2046%20Technology%20Way%2C%20Salem%2C%20MA%2001970___a_~



.42.522818_-70.882383_near%20Blaney%20St%2C%20Salem%2C%20MA%2001970___a_~



.42.533614_-70.873446_near%2010%20Restaurant%20Row%2C%20Salem%2C%20MA%2001970___a_&mode=D&rtop=0~0~0~&form=LMLTCC
Less industrial under an hours drive, may be more isolated, not sure if there would have been boats around, but interesting. This is an aerial map from 2014, both options are there for any map.
http://www.bing.com/maps/?v=2&cp=42.494570~-70.878399&lvl=14&sty=h&rtp=



.42.484582_-70.932229_Spring%20Rd%2C%20Lynn%2C%20MA%2001902___e_~



.42.511779_-70.845477_near%2010%20Beacon%20St%2C%20Marblehead%2C%20MA%2001945___a_~



.42.495340_-70.924403_near%2036%20Technology%20Way%2C%20Salem%2C%20MA%2001970___a_~



.42.492064_-70.855368_near%20152%20Ocean%20Ave%2C%20Marblehead%2C%20MA%2001945___a_&mode=D&rtop=0~0~0~&form=LMLTCC
Aerial of pin D in above map, notice anything?
http://www.bing.com/maps/?v=2&cp=42.492026~-70.855691&lvl=20&sty=h&rtp=



.42.484582_-70.932229_Spring%20Rd%2C%20Lynn%2C%20MA%2001902___e_~



.42.511779_-70.845477_near%2010%20Beacon%20St%2C%20Marblehead%2C%20MA%2001945___a_~



.42.495340_-70.924403_near%2036%20Technology%20Way%2C%20Salem%2C%20MA%2001970___a_&mode=D&rtop=0~0~0~&form=LMLTCC
http://www.bing.com/maps/?v=2&cp=42.461282~-70.929466&lvl=13&sty=h&rtp=



.42.484582_-70.932229_Spring%20Rd%2C%20Lynn%2C%20MA%2001902___e_~



.42.421936_-70.917921_near%20Summer%20St%2C%20Nahant%2C%20MA%2001908___a_~



.42.495380_-70.923642_near%2028%20Technology%20Way%2C%20Salem%2C%20MA%2001970___a_&mode=D&rtop=0~0~0~&form=LMLTCC