I've said some of this before, but I'll repeat what I said anyway...

Personally, I try to send my poetry to pay markets first, except for certain pieces that were created specifically for certain "4 the luv" markets.  I do try to send to "likely" markets first, ones that seem to like my style.  Occasionally I will write something with a certain theme for a specific market, like my submissions to Hungur (the theme of that particular market has inspired a few specific works).

I will send my more "general" works to whatever market is open and seems a likely fit (for instance, I wouldn't send a sci-fi poem set in the future or something referencing modern electronics to The Willows).  After several rejections of various styles and themes by certain markets, I'm unlikely to send them "more of the same".  I might try these markets again, but they wouldn't be my first choice, and I would have to have something significantly different from my usual to send their way.  (I'm not trying to "play editor" so much as decide how best to spend my time and effort.  Some markets are quite specific about what they will take.)

The higher paying markets may be a bit higher on my list, but only if I don't already have something in their slush.  If I do, and they voice a dislike of multiple submissions, I will send elsewhere.  I'm also beginning to prefer markets that I've dealt with already, but I'm certainly trying to break into different ones as well.  I rarely hold a piece just for a particular market because I feel it would be more worthwhile to send it out and see what happens than letting it sit on my hardrive and hope a specific market will like it.

As for postal submissions, I don't send my poetry through the mail.  It's easier to just send electronic submissions.  Perhaps I will try to send a poem to Asimov's some time, but the majority of markets that take speculative poetry take (or even prefer) electronic submissions.  

"Who dares wins" 

I aim high.  When it's rejected, I aim lower.  I don't generally waste time on 4thlvof markets because they don't look good on a resumae.  If something's not worth anything to a publisher, then I need to work on it until it is.  I'll toss it into a file to re-work when I'm better. 

I may only get a penny an hour by the time I'm done,    but I do get paid.  "Amatures give away their work, professionals get paid."  (Sometimes I kick myself for hammering out a 10,000 word story and selling it for $10., but then I have to remind myself, it's a hobby, thankfully I don't have to make a living at it.  Maybe someday, when I'm better at it . . . 

Now there are other sorts of pay than cash though.  If I see a project I like or a chance to get feedback--and feedback from honest people who like stories is worth more than semi-pro pay, I'll be glad to put in the work to submit a piece. 

I've made more this quarter than I have any year since I've been writing, so I guess the snowball just keeps rolling and getting bigger as time passes.  It must be working to some extent.   

Maybe I'll be able to claim it as a 'side business' this year rather than a 'hobby'.