Do you enter contests? I do at times, but have limited my contest entries during the past few years. Instead of sending out my work to any contest, I pay attention to the judge, his or her work and the entry fee.
If the judge has written something similar to my style, I may have a better chance of having him or her respond positively to my work. If I write fantasy poetry, and the judge has published books on fantasy poetry, then I think my work may be a good "fit."
A couple of years ago I entered a contest that featured a judge whose work wasn't similar to mine, but I submitted a piece I thought he would respond to. My strategy worked. I won second place.
I also make sure my entry fees go to contests where I get the most for my money. For instance, I check the entry fee, the prize awards, and whether or not a critique is provided. I wouldn't spend $25 on a contest that features a $50 prize. I might, however, be willing to spend a little more if I get a critique from someone whose work I admire.
Some writers vary the amount they spend every month, others have a strict budget they adhere to, and others just send out whatever they want, whenever they want. Whichever type of writer you are, try to get the most for your hard-earned dollars. And remember, if nothing else, you may be able to deduct this expense from your taxes!