Although I stopped buying new Marvel and DC comics regularly in mid-1989, and didn't begin buying them again until mid-1997, I did purchase the occasional new issue in the years in-between. But these one-off purchases didn't lead to me becoming a returning customer. For example, in Spring 1991, after borrowing a friend's recent issues, I was impressed by Jim Lee's art on Uncanny X-Men and considered buying it myself. In the end, I only bought one issue, X-Men #3 (Dec. 1991) which, as it happens, was the final issue written by Chris Claremont. (He returned years later, as did I.)
When Mark Waid replaced Mark Gruenwald as writer of Captain America, I bought Waid's first two issues (#444 & 445, Oct. & Nov. 1995) in one purchase at my local Waldenbooks. It was the first new Cap issue I'd bought since #356 (Aug. 1989) which I had bought at my local 7-11 on May 14, 1989 (when I was 18) along with Uncanny X-Men #247. However I was turned off by its in-your-face art style. I think I mailed off a letter to Marvel giving my opinion, feeling very old and out-of-touch with modern mainstream comics.
The following year, around June 1996, at age 25, I had some money burning a hole in my pocket and on a whim decided to buy a bunch of new comic books at a local comics shop, just to see what they were like. If I recall right, I ended up spending around $20 or so, which soon felt like a total waste of money when I got home and found much of what I'd bought to be unreadable joyless product, too slick for my old-fashioned tastes. I had bought a bunch of basic Marvel and DC titles that caught my eye from their covers or titles, but in retrospect I would have been better-served by being more selective and discerning in my choices, perhaps sticking with comics I was already predisposed to enjoying, such as Archie comics, Dark Horse's Tarzan or new reprints of old comics. For example, I would have liked X-Men: The Early Years, a monthly series that reprinted the early Lee-Kirby issues, but the final issue -- #17 (cover-dated Sept. 1995) -- came out several months before my 1996 buying spree. However Big Bang Comics began a new run, published by Image, around the same time as I bought the following 1996 issues, and that would have been more up my alley.
I can't remember every single comic that I bought in that 1996 haul, but here are the ones that I do recall:
DAREDEVIL #353 (June 1996)
DOOM 2099 #42 (June 1996)
GREEN LANTERN #73 (April 1996)
GREEN LANTERN #77 (Aug. 1996)
IRON MAN #328 (May 1996)
LEGION OF SUPER-HEROES #78 (March 1996)
NEW GODS #10 (Aug. 1996)
SENSATIONAL SPIDER-MAN #5 (June 1996)
SPIDER-MAN TEAM-UP #3 (June 1996)
WONDER WOMAN #110 (June 1996)
I think I bought Doom 2099 #42 because John Buscema penciled the cover. However, the art inside was by somebody else and it looked really weird -- like, even weirder than weird. So weird, in fact, that I actually kind-of almost liked it, since at least it was different and not trying to look like the popular Image artists of the moment. However, I was not inclined to buy another issue, and the series was cancelled with #44 anyway.
I'm not 100% sure that Green Lantern #73 was part of this haul, but I think it was. I seem to recall at the time thinking that GL had been retitled Green Lantern/Green Arrow by the time of #77, but this was actually only a temporary change (and only on the covers) due to a crossover with Green Arrow's own series (where the name order was reversed). Anyway, Kyle Rayner was Green Lantern by this time, and while I'm not adverse to any and all change, this particular change looked like pandering to younger readers.
Iron Man #328 was during the "Teen Tony" era, where Tony Stark was a teenager who looked like he belonged in a manga series. It looked like more pandering to teenagers (see above) and was an immediate turn-off for that reason alone. (The in-your-face art style didn't help.) Iron Man was actually cancelled shortly after, with #332 (Sept. 1996), although of course it was renumbered later and has been renumbered many times since.
I may have bought Legionnaires #37 (June 1996) in this haul as well, but can't be sure.
New Gods #10 was one of those comics where I should have looked more closely inside before buying it, because the art style was such a turn-off to me, with overly-muscled characters. If I had only waited a few months, I could have gotten #12 (Nov. 1996) instead when it came out, which not only featured John Byrne as the series' new writer-artist, but had a lower cover price (only 99 cents).
Spider-Man Team-Up #3 had a $2.95 cover price, which seemed like a lot in 1996, although it contained more pages than a regular comic (which had cover prices in the $1.95 range back then). I had liked Bob McLeod's art in the past, so I figured that I'd like this issue, too, but there were little Jim Lee-esque touches in the inking that bothered me, that looked a bit like pandering to the Image buyers. This series only came out a few times per year, and #7 (June 1997) was the final issue.
I also think that Storm #4 (May 1996, final issue of this Marvel series) and Detective Comics #697 (June 1996) may have also been in my 1996 haul, since their covers are so familiar, but I'm not certain so I left them off the list above.
As it turns out, I was a little bit too early in my attempt to jump back into the comics scene, at least when it comes to being inclined to enjoy what I had bought. In early 1997, I ended up getting a pull list at the same comics shop I'd bought those new comics at in 1996. I usually stuck to the back issue and cheap boxes there, but when I told them that I wanted to buy a new Steve Ditko series (published by Fantagraphics), which they happened to have sitting on the new-release shelf, they informed me of their pull service and signed me up. I was given a Previews catalog for free each month as long as I had one new series on pull there, and gradually I started pre-ordering new comics from the catalog.
I tried Daredevil again with #365 (June 1997) because it was now being drawn by Gene Colan, so this time I knew I would have fewer complaints about the art, since I liked Colan's work. I bought DD semi-regularly until #375 (May 1998), by which time Colan had left the book. I wouldn't buy another new Daredevil comic until #82 (April 2006) when Ed Brubaker became the writer, and added it to my pull list. I bought the series regularly until 2014 when I stopped buying brand-new Marvel and DC comics entirely.
So, in other words, when I tried again in mid-1997, gradually picking up a few new titles at a time, conservatively at first, sticking with stuff that I was inclined to like and then gradually expanding my choices over time, I got sucked back into buying new comics again. By the end of the 1990s, I was buying several new Marvel and DC titles every month, which I hadn't done since the late 1980s.
My mistake in 1996 was trying to jump in feet first, buying a bunch of random new titles based on their covers and their titles and hoping for the best. This, it turns out, was like the reader equivalent of buying a lottery ticket and hoping to hit the jackpot. More often than not, the result of such a random purchase is going to be disappointing. Another difference between 1996 and 1997 was that I'd begun posting on comics message boards on the internet in 1997, where discussion of new releases dominated the topics. I was able to get a better handle on what was coming out each week, what new titles to look for, and so forth, rather than randomly picking stuff off the shelf because I liked the cover.
So, based on my failed attempt to get back into buying new comics in 1996, and my successful attempt in 1997, I would recommend to anyone wanting to become a regular reader of new comics again to start out slow and stick with what you know in the beginning. If you like a particular character or creator or company or genre, your best bet would be to stick with them before branching out into unknown waters. There will be time enough later on to try the others, after you've become accustomed to what comics are like these days as opposed to what they were like in the past.