House 2
From your list of what it needs:
New kitchen
Clean the existing one. Live with it for at least a year before changing it.
New utility
Unless you mean 'is falling down and needs new walls and roof', this is not a priority. Stick a washing machine in there and put it towards the bottom of the 5 year plan.
New doors/skirting boards
If the doors are missing you need to buy some, otherwise neither they nor the skirting boards need to be done immediately.
Driveway widened
Looks big enough for a car. Why do you need it wider?
Garden sorted
That will also need doing in the new house. Not urgent. Very cheap.
New shower in ensuite
Needn't be done immediately if you have a working on in the main bathroom.
Fitted wardrobes
Not necessary. Freestanding secondhand or IKEA ones will do you fine for a few years.
New floors upstairs
OK, yes, this does need doing and before you move in.
New boiler
Budget around £3k. Maybe a little more if you are switching to gas, but that will pay for itself in no time. You won't be in time for the new boiler grant - it expires in mid March.
Completely repainted inside and outside
Fill nail holes with polyfiller, undercoat (stain-stop undercoat where the writing is), couple of top coats. Budget around £50/room unless you're going for designer paint. Outside I'd get the professionals in - not a job I've had done since moving to NI but I doubt it would be over £1k unless there's a lot of patching to be done on damage render.