Pros: Decent predictable power, fair two up comfort, beginners to veterans alike should enjoy this bike.
Cons: buzzy at sustained 75mph riding, cheaply & easily fixed with alternate sized sprockets.
I acquired mine as a trade in late 1998, I had a 1500 Vulcan that was a constant source of rind peeling exercises which I traded "down" for a 95 Shadow VLX. Considering the VLX hasn't shed any parts or liquids like the Vulcan once did so frequently, I consider it a trade up.
I modified mine since arrival, the stock front end was shelved in favor of 8" over forks and a 10" medium ape hanger bar all on a Seeger Cycle Accessories wide glide kit. The rear was lowered, and some forward controls added. A fair list of other add-ons could be written, but that would include the usual boring bolt on stuff most folks don't care to read about so I'll leave it at that.
Suffice it to say, it's quite the head turner.
In terms of reliability, I've only been replacing consumables for the past ten years: oil, filters, batteries, coolant, tires and such. No OEM replacement parts have been required, all of the survivng factory parts from my chopper conversiopn are still intact.
I regularly net 60-62mpg on the bike, flipping reserve at 120-130 miles. That leaves me with a generous 0.9 gallon reserve, or another 54 miles of riding time before needing a refill. The factory tank may not hold a lot, but it'll take you far enough.
In my humble opinion, the 88-98 models are superior to the more modern 99+ bikes. While the 99+ bikes sport a lower seat (25.6" compared to the 88-98 27.2" seat) Honda pulled one of the carburetors off the bike in 1999, and performance suffers as a result. It's about a five pony difference, enough to make the modern 600 in league with the 88-98 400cc Steed counterparts sold in Asia. Also consider earlier VLXes had smaller tanks at 2.4 gallons (88-93), and chromed Deluxes w/ two tone paint came out in 1994 (as well as a limited production 93 test market model).
So unless you're really inseam challenged and the first generation bikes are too tall for you, I'd say bang for your buck a 94-98 model should be at the top of the list.