Just a follow-up for those that might care (and I realize that may be no one), but I went through with getting an escort and I don't regret it.
The experience was a bit surreal. I'm not used to having a young, attractive guy show up at my door and be naked in my bed in a matter of minutes. Also, the guy I selected had done porn in the past (sites many on this board are familiar with) and I actually own a few of his videos. So, it was a bit weird to have him present in the flesh and blood.
He was really cute, but came across as being genuinely nice too (though that could have just been an act). We talked briefly before starting and it was a very pleasant and easy conversation. We moved to the bedroom and he quickly got naked...again this was a little surreal since I've never had a hot guy get naked, hop in my bed and then invite me in.
I'll admit my own performance was not the greatest reflecting a combination of being nervous and not having a lot of experience. We had some nice foreplay (though my kissing skills are not great) and then oral. My oral skills seemed to work as he quickly got hard, so that made me feel good. While turned on, I couldn't get really hard, so I had to bottom which was fine by me though I think he prefers to bottom but listed as versatile. It was a little tough at first (as he was well above average in size), but eventually we built up a good rhythm. After we both came, we laid in bed for a little bit and chatted before he headed out. I was a bit sore for the next two days, but it was worth it.
The only regret I would have was that I wish I was a better performer in bed. That takes practice of course which I don't have much of. The upside to a good escort is you don't really feel obligated to impress them. It's not like you're trying to have a long-term relationship. Though I kind of feel bad for him having to have sub-par sex with me, but at the same time I realize that's the choice he made given the line of work.
Of course, there are downsides. I'm not going to pretend this was romantic, boyfriend sex. Truth be told, I could have cuddled with him for hours (before or after the sex), but that wasn't going to happen unless I forked out a lot more money which I don't have. And I'm under no illusion that this replaces a real relationship. I still intend to try and find a real relationship, though I recognize the odds are against me.
My recommendations are as others said to go with someone that has reviews and is on the high-end side. I would stay far away from Craigslist/Backpage. My father's words were always "If you are going to do something, do it right and not half-assed." Now I'm sure he didn't have purchasing male escorts in mind when he said that

, but the theory is still a sound one. Of course, safe sex is a must too.