It took a little conversion work to get Aragorn just the way I wanted him, but after that, I was on a quest. Gandalf is a straight-up Reaper figure. Boromir was much harder, but eventually, I found a Reaper ranger with a horn. The more I looked at him, the more I began to see the possibilities. I had to cut off a weapon and add a shield, and he'd need some facial hair...
Gimili proved the trickiest of all. I think this is because I had the least clear vision of the character. In the end, I found a Reaper figure I liked. I wasn't sure I had Gimili when I finished, but a couple of years later, the figure has really grown into the character for me.
I had some Reaper minis for hobbits, but I could never quite get it to work. I could find a good Merry and a Sam, and a third figure that I could never decide if it was Frodo or Pippin. Also, the more I looked at them, the more I became convinced they were just too large, more small dwarves than hobbits. So, I reversed gears, went looking, and finally found my perfect hobbits. I got them from Scotia-Grendel, but they were originally produced as part of the Harlequin, The Lord of the Rings line. I swapped which one was Merry and which was Pippin, and gave them their movie colours to better distinguish them.
Four years is a long time to paint 9 figures (or actually 12 if you count the 3 discarded hobbits), but really, aren't these the most important 9 in the collection?
(Of course now that original Legolas is looking a tad dated... my painting has gotten better since then... maybe I should go back and paint him again...)