Okay, I've done loads of research and the reason I bring this to you guys is that I have a lot of specific concerns, and you all have a lot of specific experiences. I hope your experiences and my concerns coincide and I can get some advice. I also hope I'm not annoying with these questions. I'm about to write a lot. While consider myself a complete amateur for life, photography has become a source of income for me in various ways and I'm trying like hell to get good at it. The photos that pay me are essentially portraits. Haircuts, to be exact (see attached images to get an idea of what I do). I'm shooting on a 5D mark iii and I've always used a Sigma 50mm F1.4 Art lens or a Canon 24-70 2.8L (the first version) but I recently borrowed a friend's Canon 100mm F2.8L macro lens to shoot some jars of pomade and I only briefly fiddled with it for portraits. Then when I was on vacation in Tahoe I brought my tamron 150-600mm, hoping to get bird pictures, but while jokingly taking photos of my wife at the long end of the lens the truth about longer lenses being better for portraits, which I had read repeatedly, finally clicked. My portraits at 50mm looked great until I saw one at 100mm+ So I borrowed the 100mm F2.8 again and found that it's almost everything I've wanted (it was used for both of the attached images). The down side, is that there are what seems like a billion options for other portrait-capable lenses over 70mm, so I start running all the "what if" scenarios in my head and I start to doubt the lens that seems like it would do the job perfectly. Plus (and this is a big negative for me buying the 100mm) I can borrow this lens any time I want, so I'm reluctant to buy one. Is the older canon 100mm F2 (the short little one that looks just like their 85mm) for portraits going to get nowhere near the IQ that I'm getting with the L macro? Is the focus going to be painfully slower (this is why after renting the 85mm F1.2L I decided I didn't need it) than the macro? How about the non L version of the 100mm macro? They're so close in price, am I paying for the red ring with the L version or is it actually worth more for what I'm doing? I've looked at the tamron 85mm F1.8 several times, especially because I've grown to really trust my Tamron 150-600, but then I wonder if 85mm is going to look and feel different enough from the 70mm side of my 24-70 to make it worth the buy. 100mm is way different. I've also drooled over the sigma 85 (and upcoming 135) but in all honesty I don't trust sigma anymore, since my 50mm is the most temperamental lens I've ever owned and I've had such bad experiences (front focusing, even after repeatedly "correcting" it on the USB dock) with their 30mm Art and their 24-105mm Art lenses. The only reason I haven't sold the 50mm is that it works realllly well for me when it is in a good mood, every time I'm ready to throw it at a wall it starts behaving. I should also note that my studio is small, I can't get away with a 135mm for portraits in there unless I stand outside the door and shoot from a hallway. But in looking for a good 70mm+ lens the other biggest hardest decision comes up, because a 70-200 will likely handle this need and THEN some, but then it's like, 4 or 2.8? IS or non IS? And that's before even thinking about third party lenses. If I wait for that new tamron I'm going to pay FULLLL price (I'm usually only interested in used or discounted, but if something is amazing and perfect for me I'll pay full price) then if the lens is a flop I've lost money (not the worst thing, but it's a small concern) oh yeah, my budget is around $1,000. So by now, thinking used 70-200 or waiting a few months for the budget to grow, I remember that they're big and heavy, harder to take on the road (I travel a LOT for hair events) and the 100mm F2 becomes attractive again. Except that it's an old design that's been out since like 1991, so I worry it'll be obsolete very soon (if not yesterday), so then the macro L lens sounds right for me again, until I remember that I can borrow it when I need it, so then I think about a 70-200 again. See what I mean? So what do you think? Hopefully some of you have owned or extensively used some of those lenses and can guide me. What would you do, having more experience with this than me? Thanks for reading.