Guys -
Thanks to all for all of the insightful info. I'll respond to a few of the various comments and recommendations:
In general, yes - I agree that buying one higher quality tractor versus 2 cheaper ones over time will likely be a more rewarding and less frustrating experience.
LBrown59 re: JD Dealer opinion of new 3-series versus older JD models:
"3*He is naturally going to favor the new over the old; his business depends on it." -
Yes, I assume he will. I was thinking of calling the service/repair center, which is totally separate from the JD sales center, and see if I can't get an honest opinion out them.
jcmseven: "I think we must be careful to not graduate out of our OP's budget desires. If he is looking at a 300 series machine, he might not wish to go the full monty to an X 700 series tractor. Examples of used tractors he might wish to check out: 325,335,345,425,445 455 (though the diesel might be overkill) and don't forget the 2210 sub-c."
Ahhh...the voice of reason. With my oldest just through her first year in college ($51K a year!!!) and two more to go, being budget-conscious might not be a bad idea! That said, I will see what I can find out where I can check out any used older 300 or 400 series JDs. Not sure where the best source in my area might be for that (Morris County, NJ) - Any recommendations?
There is a JD sales and rental center locally that might have older machines, but I'm not sure that a former rental machine is a good idea.
Budlite and TigerfaninAr: regarding the current X300 series bagging capability - "6. CAPABLE bagging system, that won't readily clog. - No idea, don't bag", and "6. Bagging--don't know, never had. Last Fall I had to cut some thigh to waist high grass and it went through it much better than I thought. I'm sure like everything its not as good as the older versions but I'm satisfied."
As mentioned, I'm not a huge fan of the PowerFlow bagging unit that I had on the Scotts. It would've been fine had it had a full metal housing. It projects out far, and the plastic shields and housing wear through and fall apart over time. As I mentioned, my neighbors LA110 JD with only a 42" deck really choked on my lawn, and you could hear the engine and belt system labor when I hit the thicker patches of grass. A PowerFlow bagger for a new JD X300 series adds another $1000 to the bottom line, so I may need to factor that into the equation.
Just as an aside (and not to digress too far from my original post), my father mentioned that I should look into what's available from New Holland, since they're owned by Ford, and I can get a decent (former employee) discount. I think that the smallest thing they make is the Boomer 1020, though, which is likely way out of my league.
Thanks again - I've gotta focus on the "white collar" aspect of my work life for a couple of days - I'll advise as to what I turn up - in the meantime, I appreciate any additional comments.