Trying to pick a hotel & other travel planning

I have been obsessed with planning our trip to Ireland for a few weeks now and since it is almost just a month away my obsession has kicked into high gear. I have never been to Europe or anywhere really fascinating until this year when we went to California so it's something very new and exciting for me so I just have to obsess! I am an organizer by nature and was much more so before motherhood took my brain but I still like to have plans and ideas. I think motherhood actually gives the planner in me a more "worrier" persona as in I think about everything that can go wrong when traveling with a kid so I like to anticipate these things and plan for them as much as possible. I'd like to think that if we were traveling without a kid that I might just let us go without a plan and pick hotels when we get there but we'll have T-man and I want to make sure that when we stay somewhere it's the best possible place we could pick in terms of value, kid friendliness and other amenities.

We actually had a loose itinerary planned out with our fist two days involving overnight stays in two different towns on the way down to M's parents' house but then in true family fashion M calls his parents after booking our B&Bs and finds out they had planned a surprise trip to one of the towns for us in the middle of our trip. At first I was annoyed at this wrench in my planning because it involves driving way back up to the area around the airport right in the middle of our trip but I've been able to re-work the itinerary around it. Also, they will be paying for our room so I can't complain about that (although fuel costs over there are outrageous so I am sure I will be able to rant about that). So now our plans are as follows:
Day 1: Land in Shannon, visit nearby castle/amusement park, drive to Dingle Peninsula (~3 hrs) for overnight stay at B&B
Day 2: Drive down to Allihies (~2 hrs) and explore Ring of Beara along way, possible stops in Killarney and/or Kenmare

Next few days are spent in Allihies until we head out again back up to the Shannon area to spend the night in the town of Lehinch which is near the town of Doolin, where we originally wanted to spend Night 1. M's parents have a wedding to attend so we'll explore and hopefully not get suckered into going into this wedding. IF WE DO NEED TO ATTEND THIS WEDDING - I want to know, like YESTERDAY, because that obviously changes my packing plans and means I need to buy something to wear to an Irish wedding and possibly also bring a new liver from what I've heard about Irish wedding!! See what I mean about obsessive planner? The next day instead of heading back down to Allihies we'll drive to Cork City and stop at Blarney Castle on the way down. This is where my hotel picking has driven me nuts. There are just too many reviews out there and I want to keep costs down but I also want to be in a good spot. M hasn't been home since 2003 and he warns against scary parts of Cork and of course the hotel I love which also offers babysitting is quite pricey but I am thinking it's one night and we've just gotten one of our planned overnight trips paid for so why not? Well I've got a topic started on TripAdvisor's forums (I heart that site, btw) and their resident "Cork expert" is agreeing with me about my hotel pick so I just need to decide if we want to spend a little more and enjoy one night of semi luxury. Check it out for yourselves. The cost would be about $200 (US) without breakfast which isn't that bad considering hotels are more expensive there and to get a hotel right in the heart of NYC or Boston you'd pay that much or more! Ahh someone decide for me, do we look for something cheaper or go with this??? Magic 8-ball where are you???