My 2006 Jeep Cherokee KJ (Liberty CRD) constantly has air in the fuel head, but I was n't suffering starting issues (starts in an instant).
Every morning I can pump the primer and get lots of air out (takes 3 to 4 primes).

I already have the new style fuel head and replaced the quick connections at the back of tank (both intake and return line) with high pressure rubber hose and double clamps. However I am still experiencing air in the fuel head, so I suspect the actual fuel head could be letting air in.

My next step is to install an inline fuel pump (prefer external pump like a Carter for easier maintanence if required).

Has anyone replaced the quick connects with normal rubber hoses, and has it fixed your air in fuel issue ?

I replaced the fittings with injector line but I put in Kennedy lift pump at the same time so all I know is I haven't had any problems since. My sons crd started having to be pumped often them bleeder valve started leaking some fuel he already had a lift pump, replacing fuel head took care of whole problem.

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05 Blu LIM, OME GDE Tbo, wk II 245/75/17, KC Lights, bull bar, 195K H TC
05 Blu Lim, Dayton, GDE HT, 255/75/18 , 210K , H TC
06 Bla Lim, GDE Eco, Destination AT 245/75/17, 151K, H TC
06 D Khaki Lim 126K wkII Eur TC
05 D khaki Lim 145k refurbishing
All CRDS: Fumoto, Lift , Fan Shroud mod, fuel head Gen II, SAMCOS,self TB, 2 Mic filt, Hayden

mine did the same thing with air in the filter. it started and ran ok for about 3000 miles and then all hell broke loose. it would shutter and knock as though it was in limp mode. I stopped and bled the filter (new style) and it ran just fine. once a week I would bled the filter and always got air out of it. last Monday a carter in tank lift pump was installed. it starts quicker, runs quieter and is quieter at idle. I think my gas mileage has also gone up or I have an air bubble in the tank, went 56 miles on 1.5 gallons.
replacing the quick disconnect hoses will eliminate one potential place for air to enter the system.