No matter where you buy, please, please make sure that you don't have to depend on rentals whilst the property is unoccupied. If you are ok with that, then a major part of the battle is over.
You will have to take into consideration ease of access too and how expensive flights are all year round. Summer flights at least double or triple in some cases as you probably know already.
With that in mind, if its a bit of sunshine you are after, then countries like Spain are top of the list. Cheap and relatively short flights, lots sunshine, things to do, no language barriers. There are so many beautiful areas that have not got caught up in the concrete jungle era and still maintain their Spanish culture yet having everything you need to enjoy a break away.
Portugal and Cyprus would be similar, but it is more expensive and so are the flights.
Are you buying for you or your kids? My teenager is grumpy no matter what country he goes to but I have a 3 year old who loves the beach and playing by the pool.
As long as you can afford it and are happy with it, then go for it, no matter where it is. Yes there are a million things to take into consideration and you could follow all the best professional advice in the world and it may all be well intentioned - but as long as paying for it doesnt get you down or trying to get to it and you know you will enjoy it, thats what counts.
Take your time and dont rush into anything either way. Maybe you could use the opportunity to go on lots of holidays to several different places and get a feel for it - time to dust off the passport sweetie and get packing!