There are so many properties up for rent, that renting itself could be a problem!!
I have just stopped letting my property, mainly because I want to use it a lot more. I always went for long lets. I was told at the beginning that if you go for a long let people are more likely to look after the property, whereas when people are only staying for a week or two they are perhaps not quite so careful..
If you let your property in the peak times (short let) you get far more for it pro-rata than if you let it for a long period. However, for a long let you are sure (well almost) of getting money for x-amount of time, whereas a holiday let may only be spasmodic.
You need an agent or a friend to check on the property; make sure that you have a full inventory - and that it gets checked at the end of the each tenancy!! Hold on to the deposit until you are sure!
I'm sure that other people will have things to add to that - or maybe even different opinions!!