Hello everyone, I'm new to this forum and I look forward to all the additional learning I'll get from reading these great threads. I've already done a lot of reading in the last several days but there's so many varying opinions for so many things I just would like to get some narrowed down advice. To start I'll say what I have now, a T2i with 'kit' lens and the 75-300mm zoom I got as in a bundle. I am happy with the quality of the T2i coming from a ultra-compact point and shoot Sony camera, but I have been noticing more and more the small things with these cheap lenses and want to look into seriously upgrading aka investing in high quality lenses. For now lets say I have a good size budget because I'll save up for anything if worth it. I know the issue of EF vs EF-S lenses will come up but what I'd like to do ideally is get EF lenses because in the semi-near future(2 years or less) I'd like to get a FF camera as my final body upgrade for the foreseeable future(I'm thinking 5D but debating between II or getting the III when Canon releases a IV, still comparing specs. Any advice or experience here would be amazingly helpful). With that I'll get on to the actual questions.
My main interests are in Landscape and Macro photography, as well as a recent uprising of an attraction to portraiture after going on choir tour. I think with 3-4 lenses I can cover everything very well, this is where the big questions come in. Is it possible to have a single lens that can be a great landscape UWA lens while being a good walkaround lens? I have been really looking at the 17-40L f4 to fill that role but I have read that its an awkward lens for a crop sensor. Then there's people who recommend the 16-35L and the 24-70L but the 24 would require another wider lens for landscapes. Secondly, for portraits and an additional lens to carry when 'walking around' I plan to get the 50mm 1.4, I don't see myself needing the 1.2L because I don't think I have a serious enough need for that anytime soon, nor do I want to pay the price for it. This leaves Macro and telephoto. For Macro I'm pretty well decided on the 100mm f2.8 IS macro lens because I like the price and I'm not convinced I need the minor improvements given in the L version, nor the higher price, plus at the time being I'm not head over heels for macro so I don't want to spend that much. Lastly and possibly most controversial is telephoto. I am a big fan of having lots of zoom. With my 75-300 lens, often times for animal or wildlife shots I find myself going right to the 250-300 range usually. There's just so many choices in this area I'd just like general recommendations for that just to gauge the input.
For some final parameters of my style to help with any advice you want to give, I tend to shoot outside more than in, and I dislike using a tripod and 95% of the time I don't have mine, plus its a crappy $40 bestbuy tripod. When I do use my tripod is at night because something I'm still trying to figure out and 'perfect' is night shooting. Star/Milky Way shots fascinate me and I want to get setup so I can do that. Anyways, so outside more often, and almost never a tripod. So do with that what you will and I greatly appreciate any and all tips/advice you guys can give me to help me out. Thanks so much.

