I guess all the "real mechanics" are going to get a chuckle out of my experience, but since this was a new one on me, I thought I would share to save someone else a frustrating afternoon "monkeying around" in the wheel wells.
On the first owner assisted annual after buying my Mooney, I spent days trying to get grease into the landing gear grease zerks which had "alegedly" been greased every year. The process sometimes involved taking the joints apart and cleaning out the old, nasty grease, sometimes it was just a process of forcing clean grease through the zerks.
Subsequent annuals, greasing the gear has been relatively easy.
Until this year.
It seemed like every zerk was gummed up and refused to take the grease. A huge mess ensued because the grease went everywhere but into the zerks.
I couldn't figure out what had all of a sudden clogged all the zerks! Did I use bad grease last year? What?
Then it came to me in a flash! I changed out the "coupler" on my grease gun and VOILA! The problem had not been in the zerks, but in a worn out grease gun coupler.
So....if you have problems getting grease into all those pesky landing gear fittings....it just might be your grease gun coupler is the problem.
https://www.amazon.com/DEWALT-DCGG5701-3-Heavy-Duty-8-Inch-Coupler/dp/B00HG3B97W/ref=sr_1_3?ie=UTF8&qid=1476995005&sr=8-3&keywords=grease+gun+tips