Basically the cleanliness issue is dependant on which tattooist you go to. Choose wisely, the internet is of great use here. As a rule of thumb, holiday destinations do not have the best artists, they try to get through as many customers as they can, have only a few quite basic designs and prey on people who are, obviously, on holiday. These people behaive differently to normal (maybe because of alchohol!) and may make a hasty decision. After a week or so, when the scabbing has gone and you realise your new tattoo isn't great, you are unlikely to return back to the holiday destination to complain and these tatooists are aware of this. Having said this, I wouldn't like to tar all coastal tattooists with the same brush.
Also, look for well established tattooists. In the area I live there is a guy who has repeatedly had to close his place down and re open somewhere else under a different shop name as each of his ventures quickly get a bad reputation. The tattooist I use has been operating from the same premises for longer than I can remember.
So if you do your homework and go to an established, recommended artist you will have no worries over health issues.
As for the pain involved, it all depends on where you have the tattoo, the design of the tattoo, the skill/technique of the artist and of course your pain threshold. In my experience, the pain isn't that big a deal and certainly shouldn't be the thing that puts you off.
The main consideration should be whether or not you REALLY want a tattoo and what to have. Remember, it's there for life so don't be a slave to fashion as what is 'in' this year mightn't be 'in' in years to come. Choose the design carefully and this shouldn't be a problem. One way around this is to choose something that is personal to you personally but not including family or others. That way it will always be relevant to you.
One last thing, they are addictive!