Daniel,
I?d spend a week touring the county to decide where you want to buy. Then I?d go and chat to local estate agents to get a feel for prices and see what the local rental market is like. Go and look at other holiday let properties to see what the competition looks like, and what they are charging.
As far as finding someone to do the changeover and maintenance, I would be very surprised if you have much difficulty. Ask around in the local area, or put an advert in the local paper or shop window. In the summer months most rentals are Saturday to Saturday, but in the quieter season it?s by negotiation. (People quite often just want to rent for a weekend in the winter, and obviously if you have no other bookings you might decide to accept such a booking). Most holiday properties ask the outgoing occupant to leave by say 10.00 and the incoming one not to arrive before 1600. That gives a window of up to 6 hours to do the cleaning etc. So you need someone nearby who will do that, as required (because they won?t be needed every Saturday). You will also need someone to do general maintenance, cut the grass, order gas and heating oil, and ensure the rubbish bins have been put out to be emptied. I live in Ireland but I have a flat that I rent out in England, so I can?t do the maintenance myself. I have a couple of trusty tradesmen there I can phone who will sort leaking pipes, remove & replace defunct washing machines etc, without the need for payment in advance. They just send me the bill later. You ought to try and find someone similar near to your property, so that if there is a problem, you can ask them to go round and sort it.
Apart from Christmas and New Year, you may not get a lot of holiday lets in the winter. There can be some severe cold snaps and wild gales in Ireland then and you need someone to keep an eye on the property in case of structural damage or burst pipes when no-one is there. In a cold snap you may need them to go in and put the heating on etc.
You?ll need to decide how to market the property. You could set up your own website, or you could put it on one of the many holiday cottage to let sites. Watch them because some charge far more commission than others. Choose carefully.
Elwyn