Haha well just because I like playing around with these systems doesn't mean that I don't play sports or video games either! I hate to come of as berating you into thinking this is going to be an insurmountable task. If you work at a futures brokerage you already have a huge leg up on me because you can get exact specification on how clearing works, commissions, etc etc. as well as access to data. I presume, if your firm records its own data, theres some kind of IT infrastructure around you that can help you figure out how to database it yourself and call it into R and stuff. That's more than 90% of the folks on ET can do, including myself some of the time. Maybe I initially misjudged your level of involvement in the industry, but that's a good thing. You should have no problems crossing some major bridges that have impeded me in the past like paying 400+ a month at times for data on a college budget.
I wouldn't really say that R is that difficult to learn at all, frankly. I took my intro programming classes in C++, so whenever I look at a new language, it seems like much easier because the level of abstraction is always so much higher. If you ever have any R questions, feel free to ask me; if I can't solve them, I'll pretend they're my own and have some of my TA's look at them haha. As I'm sure you're aware, it's not like guys at Microsoft and Google are pushing out production code in R; its strength is abstraction and ease of use, it's weakness is speed, and flexibility. I realize that I'm...again...sounding like an elitist, but I totally understand that programming is very difficult to learn on your own. I spent a lot of time teaching myself before I got to college, and even now I get embarrassed regularly during interviews because I have huge holes in my knowledge. I've been through the frustrations that you're going through learning, and what I'd tell you is a) it's totally normal b) don't to be afraid to ask c) preserver. Stackoverflow and sites like that might seem daunting at first, but those doods put their pants on one leg at a time too. When I started asking questions and built up a little network of friends online and around school to help me solve programming questions, it really helped me. Just ask. Literally the worst thing they can do is close the thread haha. If you want even more online help, you can use python with/in place of of R. There are plenty of people using python for all sorts of things, so finding help and youtube videos will be even easier. I don't personally use it much, but people love python.
Put bluntly: the level of difficulty of this process is directly related to the level of abstraction/control you want in your trading systems. Do you want to trade higher timeframes and not stress execution or any of that? That's easy. Do some data analysis in R, and code up your findings in something like ninja or amibroker, backtest it, and trade it. That kind of process could take you only a couple months. The flip side of that, is if you want to build something more similar to what a prop trading desk or a similar entity might deploy, you're looking at reinventing several of the 'wheels' that come with a platform like ninjatrader etc. With your currently learning curve, that might take several years, honestly. Just be honest with yourself and your objectives. I'm one of maybe 10 people actively posting on this forum who are hardheaded enough to try to build a lot of this stuff themselves, but there are hundreds of people here who will certainly line up out the door to tell you how profitable they all are using some of the off the shelf options. I have sort of a different paradigm than most of the people here; where they look for software or tools to perform a task, I look at the software and ask myself 'what are the limitations?', 'could I come up with something better?', 'will I understand how it works if I don't build it myself or see the source code?', and (of course) 'how am I supposed to afford this?!' for a lot of the higher end offerings. That's just personal preference...it often holds me back. I'm not saying that it's necessary, in fact I'm really saying just the opposite.
Also, I love that one of your goals is to get to a level of competency where you can collab with others in this field! This site seems to give such an austere and negative vibe, whenever anyone purposes a project, more people come to bash the idea than to help haha (granted a lot of the ideas I've heard on here for projects are...far fetched). That's just the nature of trading I suppose, it attracts a lot of people who believe they're right more often than other people kinda by definition, right? I personally have benefited greatly from folks on here and elsewhere who offer information and have more of a team/collaborative attitude. It will serve you well as you progress. If you want to collaborate on anything, don't hesitate to PM me and I'll happily consider participating or offer advice. I think part of the reason this site is so dead is this pervasive dick measuring attitude in trading circles. I think if we as a site are collectively more welcoming and collaborative we'll probably all benefit. Anyway, let me just also quickly say, don't be afraid to start collaborating with people now. No one's gonna tell you your help isn't wanted no matter what your ability is. People tend to exaggerate their abilities on the internet. Your level of R competency is probably not that different from mine, and mine probably isn't that different than some of my professors, etc. etc. Don't be dissuaded by what you see on the internet, as long as you stay grounded about your abilities and legitimately want to help, no one is gonna turn you away from a one of these trading projects...it's not anyone here is writing Boost or some big open source project with top notch contributors or something.