I agree with the above posts, research your tattoo artist carefully (I like the ask people who have good tats who did them approach, most people are happy to talk about their tats). The good artists are willing to work out a sketch for you and tweak it however you like. If you like the owl, then go for it! It's about what is important to you, not for anyone else. Remember that you do get what you pay for... and a tattoo is going to be with you forever, so spend the money the first time and have it done well.
I have a few tattoos, I haven't found them to be particularly painful (except the one on my ankle, going over the bone hurt, but not excruciating). I've heard sensitive areas, like the underside of your arm or rib cage can be more painful too, but if you're going for the bicep or your chest, it's not that bad. I recommend getting it somewhere that you can easily cover up in case you need to for a job or wedding or family reunions or whatever. Though they do make really great makeup for covering up tattoos these days.
I have a few tattoos, I haven't found them to be particularly painful (except the one on my ankle, going over the bone hurt, but not excruciating). I've heard sensitive areas, like the underside of your arm or rib cage can be more painful too, but if you're going for the bicep or your chest, it's not that bad. I recommend getting it somewhere that you can easily cover up in case you need to for a job or wedding or family reunions or whatever. Though they do make really great makeup for covering up tattoos these days.