Which first, D2 or D2-LOD

[Crystalion]

I am pretty new to all of this

Attempting to adjust reply, wish me luck ;)

a friend got me hooked on Diablo about a month ago.  Amazingly, after the amount of time I spent playing, my wife bought me the Diablo Warchest for my birthday

Mind boggling.

I am still playing D1, but am also going to try D2.

D2 is considerably more complex than D1 and D1 is very complex, by most people's standards (see Jarulf's guide to Diablo and Hellfire if you wish to persue that). By all means finish at least nightmare (multiplayer solo via ipx option) difficulty in D1 before moving on, in order to get the feel of the genre. You should definitely play the final (v1.09 iirc) patch in D1 (unless you decide to become an expert in such matters, in which case non-Blizzard patches and mods are open for discussion).

As for D2, I'd have to recommend using LoD if only because I think 800x600 screen mode play is a big improvement. YMMV. All of the patches for D2 have flaws (and v1.10, which you may have gathered is still in progress, is no exception, thus far). The key thing is that most people will not be seriously affected by these flaws. If you become expert enough to make such distinctions, you will probably also not need ask such general subjective-answer questions.

D2C and LoD are often quite enjoyable for characters/builds that play only normal and nightmare difficulties "well", so most people really don't need expert advice on how they "must" proceed, lest their character prove to have shortcomings in the (very) long run. Almost everyone, including experts, will "discard" their initial character(s) (albeit with fond rememberance) and move on, attempting to tackle the game anew with newfound knowledge or theories about how to play better.

In other words, just (do whatever comes naturally to you in order to) have fun. You can't make a "mistake"--unless it would be to overplay and so try the forbearance of your unusual spouse.