Sounds good. The women that are there closer to closing time are usually the ones who are there to meet somebody.
I probably wouldn't bother with the street. You might be seen as a nuisance for getting between them and their destination rather than talking to them AT the destination.
Overall, it sounds good. Personally, I don't like the word "cute", as it sounds a bit childish - I like the word "gorgeous". It's not nearly as trashy as "hot" or "sexy" and has some class to it while not being as overly invested as calling her "beautiful" or something. Just don't get caught up in talking too much to fill the silence. If an interaction is going well, don't talk, just do fun sh** - take a shot together, bring her to the floor to dance, go in for the kiss, etc. Basically, try not to talk yourself out of a lay because you don't know she's interested in you and wants you to make a move.
If that happens and the girl you like doesn't make any effort to intervene/stop the friend/continue talking to you, then just let it happen. She's probably not interested enough, and even if she is that friend will be a headache all the way to the bedroom - if you even make it that far.
You don't have to do anything crazy when it comes to clothes - just wear things that fit you snugly without being too tight or too small, and you should be fine, so long as you're not sporting K-Mark brand shoes or something. 90% of the time, my outfit consists of a well-fitted solid tee shirt (usually black) with no logos, straight jeans, a thin gold neck chain, and a clean pair of Nike Air Jordans.
I can't really speak on the hair because I'm white, and I don't do anything special with mine, so as long as what you're doing works for you.
It sounds like you would benefit most from tightening up your diet and exercise routine. What I do is extremely stringent, but I can share it if you want. Otherwise, intermittent fasting, eating at a caloric deficit, going to the gym 3-5x per week, and doing 20 minutes of cardio per day would probably do you wonders very fast.
Ok, good, we're here to f*** girls we want, not hit an approach quota.
Well that's everybody. As you saw in my other thread, I'm failing plenty and need to find some successes since my FWBs all kinda fell off at the same time. That'll come with time and exposure.
One thing you could do to get comfortable being solo without a wing is to become a regular at 1 or 2 of your favorite spots that regularly have the kinda girls you're looking for. Befriend the bouncers, the managers, the bartenders, whoever. I did this unintentionally by being friends with the manager at that local college bar from back when I attended school there, and he would let me skip the lines any time he was working. I got to know the bartenders who worked those days and would frequently tip them well - now I quite literally have to throw my money at them for them to take it, and I'm often served before all others if they see me waiting. Beyond that, the fact that I was always skipping the lines meant the bouncers began recognizing my face and got to know who I was, so a lot of times I could skip the line without even having to let my manager friend know I was there.
Basically I'm saying to make friends at the places you're going to be, because it is some serious social proof when girls see you get served before them and watch the bartenders reject your money. Plus, since you're in a bigger city, you'll have options - unlike me with the college bar.
Personally, I'd only consider Thursday - Saturday as being worth going out, but if you're getting results on those other days and can afford that frequency, keep doing what you're doing. Just make sure you're not focusing too hard on this and neglecting other important aspects of your life.
As far as your verbals and bringing women home, picking up on those cues will come with time. You'll get blown out a lot, and you'll get maybes a lot, but it's really important you know how to recognize a sure thing so you don't ruin it by taking things too slow. I've recounted this story before, but I saw a really gorgeous girl moving through the crowd with her friend one time a few years back and stopped her to tell her I thought she was gorgeous. She stopped, let her friend go on without her, sat down with me, and gave me a longing silent stare any time I was talking. I recognized this, so I went for the kiss early, to which she was super receptive, then asked if I wanted to leave with her. This entire interaction lasted maybe 20 minutes - I remember because until I saw her, I wasn't interested in anybody and invited an old FWB to meet me at the bar (she wasn't happy when she got to the bar, and I told her I'd already left). So, learn to recognize and take yes for an answer.
Beyond that, it just sounds like you need to work on your physical appearance. It sounds like you're in an OK place, but you'll probably improve your results fastest just by presenting yourself better to these women - I think that's what will have the greatest ROI for you.