I mean, how do you even begin?
Where to Start?
If you go back to the beginning of your favorite characters, chances are you will be paying through the nose to acquire most first appearances. If you start with modern comics, you will miss decades and decades of rich, character-developing story-telling that has evolved those characters over time.
And wait, is Peter Parker Spider-Man, or is Miles Morales Spider-Man? It's all very confusing to jump into.
To that end, I have developed a short list of comics that will get a new collector started. I wanted to get the new collector some key issues that stand the test of time and also pack a historical punch. I also assume he or she does not have limitless disposable income. Any collector can hop in and grab these comics for less than $1,000.
Factors to Consider
In factoring which comics to choose out of the literally hundreds of thousands of options, I considered three variables:
Iconic Characters - There are some truly great comics and storylines that feature Moon Knight. But does he have the iconic status of a Spider-Man, Avengers, or Wolverine? Most people would say no. Not many people got into comic collecting because of Moon Knight. Thus, he would get less of a priority than the old-school big boys.
Historical Significance - There are some moments in comic history that stand out to experienced collectors as truly significant. The introduction of a major character, villain, or storyline, for example. These often translate to popular comic issues and provide a low barrier to entry for a new reader or collector.
Strong Story and Famous Artists - For this one, I'm assuming new collectors want to actually read the comics they buy. There is no shortage of iconic stories drawn by famous artists: Claremont's X-Men, Miller's Daredevil, Adams' Batman, Perez's Crisis on Infinite Earths, etc. Getting some exposure to these legends earns bonus points.
To diversify the list, I chose two from Marvel, two from DC, and one independent comic.
Marvel
Amazing Spider-Man #252 - So much history in one issue as well as providing a bridge to a more modern era of Marvel comics that includes Venom, Carnage, Symbiotes, Knull, and anti-heroes.
To start, his is considered to be the first appearance of the Spider-Man black suit. There are competitors for that honor, but none are part of the canon of the original Volume I of Amazing Spider-Man. The cover is also a famous swipe of Amazing Fantasy #15, the first appearance of Spider-Man, which has since been swiped ad nauseam since this issue was published in May 1984.
In terms of story, this issue picks up right at the end of Marvel's seminal 1980's mega-event: Secret Wars. Spidey will keep the suit for the next 48 issues until Venom famously comes along in issue #300 when Peter Parker decides it's time to go back to old blue and red.
X-Men #101 - If we had an expanded budget, we would probably look to Giant Size X-Men #1 or X-Men #94, but in terms of significance to the team, this issue might be the next best thing.
Chris Claremont, beginning in X-Men #94, took over a team and a book that was struggling so badly that the previous 26 issues were reprints of early issues of the X-Men. Getting a new team and a clean slate allowed Claremont to take mutants places they had not been before. It also introduced us to the team and stories so many 'X' fans know today.
This issue also introduces the iconic Phoenix character that would become part of the series for years. Phoenix has been a key part of any X-Men story on the big and small screen. Days of Future Past, Dark Phoenix, New Mutants, and many more storylines came from Claremont's brilliance, but this is the one that started them all.
This issue recently sold a raw FN copy on eBay for $254.
DC
The Dark Knight Returns #1 - We all know Batman. We know who he is, his identity, his origin, and his setting. We 
Frank Miller had already made himself famous by revitalizing Daredevil for a period in the late '70s to early '80s. He and fellow co-artist Klaus Janson were tapped to tell a new Batman story in 1986. They did not disappoint.
The short-run of The Dark Knight focuses on a retired, 55-year old Batman. He is forced to come out of retirement to confront the evil forces of Gotham while facing resistance from authorities all along the way. The four-issue run reintroduces Joker, Two-Face, Selina Kyle, a new Robin, and even a showdown with Superman.
In terms of capturing the entire Batman universe, this mini-series stands above most others for its depiction of the true Dark Knight. Its stories were even copied many times over in Christopher Nolan's Dark Knight trilogy of films 20+ years later.
A first print CGC 9.6 sold in early October for $220 and is a solid investment buy. Then pick up a third printing NM- raw copy to read for $10. I bet you end up buying the other three in the series.
DC Comics Presents #26 - I don't know if you have noticed in pop-culture lately, but the Teen Titans are everywhere. For DC fans, they are the younger generation's Justice League but with more toys, TV shows, and movies.
This story became instantly famous and was continued in New Teen Titans #1 the next month, where the team officially forms for the first time. This version of the team remains wildly popular to this day. It is all thanks to a reimagining of the team 40 years ago.
A VF raw copy sold earlier this month for just $90 on eBay.
If you're feeling like spending up, the first appearance of the original Teen Titans occurred in Brave and the Bold #54, which has become a Silver Age Classic.
Independent
Walking Dead #19 - Choosing just one independent title is probably the hardest part of this whole exercise. You have Image, Hermes, IDW, and so many more that produce quality books; too often under the radar.
In the battle of the most popular independent series of all time, it is likely a cage match between Walking Dead and Spawn. While Walking Dead has become a cultural phenomenon, Spawn is about to publish its 311th issue in late 
Both series have iconic and desirable issues. Why not look at the first appearance of Michonne as our entry into indie collecting? Her dark introduction to the AMC show mirrored her first appearance in this comic. The katana-wielding walker-killer has intrigued readers and watchers alike for years.
While the comic and the show are both at their respective ends, we know we have more Michonne coming by way of movies and one-shots from AMC. This gives this book a chance to increase in value in the years ahead.
The first print is a lower print and more desirable to collectors. An NM- raw copy recently sold for just $210.
What Did I Miss?
For $884, this is a solid way to start any collection, in my opinion. A new reader would be exposed to many of the most iconic characters in comic history. They would possess some of the best art ever produced in comics. They'd also have a decent amount of uniqueness from which to kick off a collection. Hopefully, they would be engaged enough in the stories and characters to start the hunt for more.
It's just one man's opinion, however. If you were starting a collection from scratch or had someone ask you where they should begin their comic journey, what would you tell them? Let me know in the comments.
