Help porting Windows programs to a native OS X App? Possible for beginner?

So here's the thing. My sister bought this Japanese imported book and it has extra content in the form of a Windows program that runs these little "desktop buddies" all over her screen. She loves the buggers. I'm looking for a way to port the programs over to her OS X system as sort of a birthday type gift.

I've tried converting them with WineBottler and other apps, but they run with black boxes around them and the audio won't play. When you click them or place them next to each other they're suppose to play special audio samples and "converse" with each other. They're not suppose to interact with the windows or junk like that.

I know absolutely nothing about programming. My niche is graphic design and video. Not programming so I could really use some advice.

Can anybody suggest an application I've overlooked during my hours on google? Is this something I can even manage on my own? Do I need to find a service? Anybody willing to help me out pro bono? Is this the wrong forum section?

The file she gave me has 17 files: 8 .exe, 8 .ini, and one .dat

First of all my respect for why you are wanting to do this.
I don't know about these programs, but your best shot would be to get your hands on the source code. Then modify for Mac. Having said that, I think it is going to be hard to achieve that legally.
Another option is to create your own version of the buddies and build them directly for Mac. I am sure she will be eternally thankful. Thing to watch out for here is copyright and trademarks .... if any.
I know there are a few members on here who are into programming and have a lot of knowledge so wait a few more days and I am sure there will be more suggestions coming.

Cheers ... McBie

Unfortunately running your Windows application with WineBottler or Parallels, or even VMware Fusion, doesn’t make the application a truly native Mac OSX application, although it may appear to be when it appears on your Mac’s desktop, the program is actually running in a kind of virtual Windows window.
So the screen buddies you are referring to are in these virtual windows, which have a square or rectangular border, which is what your seeing with the black border, the window border won’t be visible when running on the Windows operating system although it is still there, so this means that the application will only truly run in a native way on the operating system it was designed and compiled for.

So this leaves you with only two other options, firstly you could install Apple’s Boot Camp software, and then install one of Microsoft’s Windows operating system on a separate partition on your Mac’s hard disk, and then use Boot Camp to start your machine with either the OSX or Windows operating systems, which in essence means you have to operating systems installed on your machine.
This option might be considered a complex overkill to run only one Windows application, and I’m not sure I would want to go this route, and leave your sister with a complex situation of having to decide which operating system to boot to when she starts up her Mac machine.

This leaves you with an option that McBie has eluded to, and that is to rewrite the application in native Apple Mac code, which as a novice developer would be a massive undertaking, and a steep learning curve if you’ve never done any programming before.
It’s unlikely that you will be able to locate the original source code for the application, but it might be worth trying.
It’s also likely that the programming language that the application was originally written in may not be a native Apple Mac language, like Microsoft’s C# programming language for example.
If it where written in the C++ or Java languages, then it could be modified and re compiled to run natively on the Mac, but again this would be a big undertaking for a novice programmer.

I assume you’ve visited the Book’s web site or support page, and checked out if there is a Mac version of the Book’s extra content software, if you haven’t then that would be a good starting point before checking out the other options listed above.
If there is a web site associated with the Book’s software, then it might be worth posting a link to it so that other members here could look into it on your behalf.

So in short, there’s no really simple solution to your problem, and I can only sympathise with you, and feel frustrated that you are unable to provide your sister with a great and thoughtful birthday present.
But do post a link to the book’s web site or support pages, and then the other forum members like myself could visit it and investigate the possibilities in more depth.

Regards Mark

Thanks to both of you for replying.

I was afraid that the answer would be like what Mark FX described. Sounds like if I really wanted to do what I plan on doing the option would be to make them from scratch. I don't think the source code is available anywhere. I can always try learning how to make apps, but I probably wouldn't be able to get them to her any time soon either.

It's from that swimming anime show. She's nuts about it. :/

The sites she gave me for the information are:
¡üTV¥¢¥Ë¥áFree! Illustration WORKS - µþ¥¢¥Ë¥·¥ç¥Ã¥×¡ª
�TVアニメ「Free!�】Illustration WORKS | 京アニショップ�
They're in Japanese, but Google Translate seems to work well enough for the important parts.

I looked around the best I could and couldn't find a Mac version of the application. Apparently somebody somewhere in the world has already shared the original Windows program(s) online. My sister gave me this link for the program(s): https://mega.co.nz/#!t0EE3RqA!fFCS7Uth5tu4dNWlp54lfSSb-YgfvFi03pEOx6XBVk0

If anybody can lend a helping hand it would be great and if not then that's understandable too. I know it's not exactly something that piques the interest and it'd probably be quite the undertaking.

Thanks for the replies thus far. They've been very helpful.

As I suspected the application has been compiled for Windows only, and the links you've provided dont give you access to the programs source code, which is a real shame.

The two operating system option would seem to be the only native option, unless you can live with the black border, neither of which are ideal situations.

Your correct in the assumption that learning the skills to write such a sophisticated application would take you some time and effort, and would possibly take longer than your sister's continued intrest in these cartoon characters, but learning a bit of programming is always a worthwhile endeavour, even if you have no ambition to become a serious software developer.

Sorry I could not be of more help.

Regards Mark

I suspected as much. I can capture everything visually (the animations) and the audio clips myself, but as you mentioned learning to write a script to make them wander around the screen, interact, etc. will likely take me a long time. Well, I'll try to learn a bit for now. It will probably come in hand in the future.

Thank you again for the informative replies.