What about some debugging & disassembling levels?

I think this is a pretty interesting topic… if you really like these things you are lucky because there are many websites dedicated to crackmes and reverse engineering in general out there :D

The only problem I can see in this is the download. It’s highly possible the download won’t work for all devices, and it won’t work on future OS types.

But it would be cool if that worked

This is how it usually is. Things are made of one platform only. But that shouldn’t stop a decent hacker. :)

You can also do many things in JavaScript if you want. Just not the platform specific things. (Unless put a lot of effort in it.)

Might also be a challenge in the challenge ;)

Well for this to be an acceptable challenge for most people you’d need stuff that’s leak already (You know I am talking about you, .NET framework).
Using languages like (Object-) Pascal, C, ASM, etc would be way too hard for most users on here. (Not talking about the pro’s and masters of the art.)

Though Object-Pascal is multi-platform and does not require anything like frameworks and making it work on most common OS' would be extremely easy (Using Lazarus with FPC), it is extremely difficult to retrieve the full source, public functions/procedures are easy, but everything that’s private/internal is nearly impossible.
So far I haven’t found any reverse engineer capable of retrieving that source, I am not able to do so myself either.

Thinking of it, might be interesting for a challenge?

Retrieving the source is normally not possible because it simply isn’t there. You can partially reconstruct it if you are lucky. Compilers, when not doing a lot of optimisation, often generate very structured code that allows this. However, I don’t see a reason why private methods would be any harder than public ones.

Of course, a good hacker doesn’t need any sources anyway. ;)

True that, and apparently it is hard for some languages. O.o
And yeah…. that’s a fact. :D

Omg, Object pascal… it reminds me of my IT studies at school…. nostalgia :s

Nostalgic but on a hard comeback due to it’s multi-platform support by default.
Embarcadero is even pushing out new IDE’s like they are loafs of bread.

The problem with this is this takes an entire other set of skills, and programs that the person may simply not have.

Also, you have security you have to think about.

Giving the security isn’t a problem, I’m up for this