So You Want To Be Tricky Like Me?
Forensics and Cryptography are the key!

Step 1: Get your tools.
http://www.gpg4win.org/
http://sourceforge.net/projects/gnuwin32/?source=typ_redirect
These two packages contain everything a windows user needs to get
started. Mac/Linux users should already have them installed or can
get them very easily.

Step 2: Set up your puzzle.
I choose to do this as a Russian doll setup. Each puzzle contained
another puzzle which contained another and another until you reach the
answer. So it went like this each level had an encrypted file and
a hint. Upon cracking the puzzle you use the password to decrypt the
file and move on.

Step 3: Doing it for real.
The way I went about this was relatively simple. I zip each folder and
encrypted them using gpg so
"gpg -c Box#.zip"
produced the next encrypted level which was then zipped and encrypted again.
For the final level when I wanted to set the password I took the sha1sum
of the photo I provided
sha1sum photo.jpg
and used that as the first level password. Then I posted the pic for you
folks to solve and put a not so subtle hint in my first post. Of course
this is where I goofed as moot's site changed my file a bit and made the
sha1sum different. For future reference directly provide the link to the
photo if you want to do this.

Solving It.
Take the sha1sum of the image I posted and decrypt box1.zip.gpg.
Unzip box1.zip and you'll get box2.zip.gpg and hint2.txt
Hint2 looked like this
8-12 2-12-6 14-26-23-22 18-7 7-19-18-8 21-26-9 22-19? 4-22-15-15 18 8-6-11-11-12-8-22 2-12-6'9-22 13-12-7 26 25-26-23 23-22-7-22-24-7-18-5-22 26-21-7-22-9 26-15-15. 12-21 24-12-6-9-8-22 18-21 2-12-6 4-26-13-7 7-12 25-22 12-13 7-12-11 2-12-6'9-22 20-12-18-13-20 7-12 19-26-5-22 7-12 23-12 25-22-7-7-22-9. 4-22 26-15-15 16-13-12-4 7-19-26-7 25-26-7-14-26-13 19-26-8 10-6-18-7-22 7-19-22 9-22-11-6-7-26-7-18-12-13 26-8 26 23-22-7-22-24-7-18-5-22 12-21 24-12-6-9-8-22 19-22'8 14-22-7 19-18-8 14-26-7-24-19 25-22-21-12-9-22. 9-18-23-23-15-22 14-22 7-19-18-8 4-26-13-13-26-25-22, 4-19-26-7 20-9-12-4-8 25-18-20-20-22-9 7-19-22 14-12-9-22 2-12-6 7-26-16-22?
Those unfamiliar might be stumped, but it's a simple numeric subtitution
cypher that reveals this
HL BLF NZWV RG GSRH UZI VS? DVOO R HFKKLHV BLF'IV MLG Z YZW WVGVXGREV ZUGVI ZOO. LU XLFIHV RU BLF DZMG GL YV LM GLK BLF'IV TLRMT GL SZEV GL WL YVGGVI. DV ZOO PMLD GSZG YZGNZM SZH JFRGV GSV IVKFGZGRLM ZH Z WVGVXGREV LU XLFIHV SV'H NVG SRH NZGXS YVULIV. IRWWOV NV GSRH DZMMZYV, DSZG TILDH YRTTVI GSV NLIV BLF GZPV?
which is actually an atbash encrypted message. Pretty easy to do as this
is stupendously old crypto. This site http://themysteryofgravityfalls.com/
is a great resource for these. Once you've fully decrypted you've got
SO YOU MADE IT THIS FAR EH? WELL I SUPPOSE YOU'RE NOT A BAD DETECTIVE AFTER ALL. OF COURSE IF YOU WANT TO BE ON TOP YOU'RE GOING TO HAVE TO DO BETTER. WE ALL KNOW THAT BATMAN HAS QUITE THE REPUTATION AS A DETECTIVE OF COURSE HE'S MET HIS MATCH BEFORE. RIDDLE ME THIS WANNABE, WHAT GROWS BIGGER THE MORE YOU TAKE?
Which of course is a hole.
Decrypt box2.zip.gpg and you get Hint3.txt and Box3.zip.gpg. Hint3 looks
like this
Vr brx'uh ilqdoob khuh dqg wkdw'v juhdw. L'p yhub haflwhg dqg kdssb iru brx. Wkhuh'v rqob rqh wklqj eorfnlqj brx iurp zkdw brx zdqw dqg wkdw'v ghfrglqj wklv. Zkdw'v wkh rqh wklqj hyhub frplf errn qhug kdwhv dqg wkh rqh wklqj d ehjjdu krshv brx wr vsduh?
But once again if you've ever played around with ciphers is easy to see
as a caesar cipher. Use http://themysteryofgravityfalls.com/ to get
So you're finally here and that's great. I'm very excited and happy for you. There's only one thing blocking you from what you want and that's decoding this. What's the one thing every comic book nerd hates and the one thing a beggar hopes you to spare?
Which of course is change. Decrypt and you get
You did it and I couldn't be happier.  Post this phrase next to your list and expect a gift.

That's all there is to it!

"Look up in the sky it's a bird it's a plane it's Santa!"