I purchased an Enfield factory lemon about 18 months ago. (If you view my posts you'll see the whole story.) I bought it from a dealer that CMW (the US distributor) doesn't authorize to do warranty repairs (because they are unreliable), and when I bought it I didn't know enough about motorcycles to do repairs myself. (I've since learned a ton.) In the first year, the bike needed major service four times (transmission failure, gas tank leak, major electrical failure, chain/sprocket), and had almost a dozen minor but urgent problems, including parts falling off on the road that needed to be immediately replaced.
However, I'm still happy with my experience. CMW stood behind the bike and authorized the necessary warranty repairs without delay. Kevin himself (the president of CMW), who reads this forum, intervened personally once when I needed him to. I found a dealer that I trust, and now I've found a second. For the most significant problem (an internal failure inside the transmission) I didn't have to pay a penny, even though the transmission had to be disassembled three times (!) in order to fix it properly.
The only significant thing CMW didn't pay for was the new chain and sprocket, but to be fair I didn't ask them to. I can't be sure it isn't due to my letting too much time elapse between adjustments, and/or continuing to ride for hundreds of miles on an already-failing drive system. (In my defense, I had no choice; the failure happened when I was on a long trip away from dealers.)
The lack of a widespread dealer network is inconvenient. The two dealers available to me are 40 and 70 miles from home, respectively, and dropping off/picking up the bike is a 4- to 5-hour round trip involving a long train ride. It's an enormous pain in the ass. But the dealers love the bikes as much as the riders do, know how they work, and treat them respectfully.
And this forum is invaluable. More than once it has accurately advised me as I diagnosed a problem, including once while I was standing by the side of the road with my tools out and part of the electrical system disassembled.
Especially given that you have some wrenching experience, you probably won't be sorry, since you can do routine maintenance yourself. Even I now do things like oil and filter changes and chain adjustments myself, and eventually I'll graduate to more major maintenance. (My other bike, bought after the Enfield, is a 100cc scooter; I'm already doing more major work on that one.)