As others have said, the main things and most important is what you want to spend most of your time doing, what life style you are use to, and what your monthly funds are. The thing I have seen happen many times over the years is guys moving here thinking they have to live in this area or that area. Then after a few months here and learning more about the different areas and (most important) life in Costa Rica, they realize they would be better off, and happier, in another area.
There are many who move here thinking they have to live in the gulch or very close so they are always close to the action where they are going to spend almost all their time. For some of those it worked out. For many more it becomes old and boring after a while. Living in the gulch means either "old and run down but cheap" or nice, modern, and expensive!!! It also means noisy, and in my opinion, much more dangerous than many other areas, and dirtier than many other areas.
There are many nice residential areas all around Chepe as other have mentioned. But what works for one may not work for the next guy. What I recommend to guys is to look for a small livable place fairly close in and preferably without a lease (hard to find but there are a few) where you can live for a few months till you have a better feel for where YOU want to live.
I had the advantage of having visited here for 10 years and having known people here (Ticos) for all those years. I had visited almost all areas around Chepe, I had input from friends who knew me, and I knew what to expect living here (I thought
) As with anywhere, life is never 100% what you expect it to be. But because of working with Latinos for 30 year, having spent a lot of time here, Mexico, and Colombia, and having been married to a Latina, I do feel I was a little better prepared for life in CR than most.
In 8 years I have lived in 3 different apartments, all in San Pedro which is the only place I ever really looked. But things have changed and I am now thinking of moving again. Why? though San Pedro is close in, has a lot of shopping and things to do, is safer than many areas, is cleaner and more modern than many areas, it is also for those same reasons a very popular area to live. Traffic has become terrible most of the time everyday and forget trying to get home between 4:30 and 7 pm if you live anywhere east of the Mall. This is actually true of a lot of areas around Chepe. My first place was a two bedroom furnished in a condo building for $450 plus electric, cable, and internet. It is now $600 a month. The second place was a very nice and very large 2 bedroom/ two bath/ furnished with a sun room and a private garden area that was $900 This was really a bargain price - it had been $1000 but because of construction next door they had lowered the price. Both were close to the Mall and 10-15 minutes to the gulch. I now live much farther out in a totally Tico area that is very nice and safe in a very small 1 bedroom place that is actually the maids quarters of a large very modern home (main house has 6 bedrooms and 5 baths) $475 including all utilities, cable, and internet. It fits my life style today as I go to Chepe maybe 2-3 times a week (bus stop 1/2 block form the door) but I spend little time in the gulch.
A couple of other things that I feel are important are: How good is your Spanish!! Living in an area like where I am and not speaking the language I would think would create a lot of problems. What are your needs in terms of food--where I live there are several small "Tico sodas" but no fast food place nor American type places. But there is a supermarket a block away. What about bringing chicas to your place? As has been mentioned, if you live too far away the taxi can get expensive. But most important--many landlords (especially if they live close) will not like it if they see you bring chicas in all the time. There are several places here that do not allow guys to bring chicas in at all. Be sure and ask!!! Another thing that often happens here is they will raise the rent if it is a Gringo looking. Using realitors that "specialize" in finding places for Gringos will almost always be much more expensive than if you found the same place on your own. If possible get a Tica to do the calling for you and have her get the price. Even then when they find out it is a gringo they will try to change the price.
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Old and retired but still bang, and bang, and bang!!!