Welcome SummitJeep, From a Former Jeep owner gone LR.
I traded my CJ-8 Juggy for a fully loaded/lifted set up 1994 D1. 4 months later I'm daily driving a 2006 LR3. I'm glad I made the jump HOWEVER....
I had more of a Buggy than Jeep at the end (Owned the Scrambler for 15-16 years) and really wanted to sell it. Nobody would buy it so I took a trade offer (the D1) because it met all the criteria I wanted, Windows, Heater, Street legal, ready to drive.
I was also offered a Cherokee (bleech..) and a 4 Runner.
Like you I've always liked the idea of Land Rover ownership. What I've found is the LR community is great, there is a lot of information available (see Disco Mikes sig for links to shop manuals). Then there is the vehicle itself. In my case the D1 came with an old man Emu lift, as well as a rear locker. So I am still able to run most of the trails and logging roads I've been driving on for years. Sure I can't take all the "Extreme lines" but I have already done all that so no big loss there. With the D1 the ride is great, with the D3 the ride is F'n awesome! (I don't wheel the D3) the D1 gets around, has solid axles front and rear, are plentiful (compared to the overpriced Defender) and have lots of aftermarket options.
What I'm getting at here is if you still want to run trails that might cause minor body damage (from low hanging branches, etc..) go for a D1 since they are more common and can be had cheap if you look on Craigslist enough. There are more than one brand of lift kits available as well. If you just want a unique wheeler to go to the mall with the Defender is a good option but getting into one isn't an option for under 5 figures.
I've been happy after my switch, and all my buddies with their Jeeps are surprised that my Disco goes so well. I just laugh at them from behind my windshield and comfortable heated environment.. LOL.
In a few years I'll take my D3 on a trail run, but not now, it's still to nice!