How do you decide where to buy?

That's a great question.  It will also be a very personal choice when you start really looking at areas, whether domestic or overseas.  This blog is geared to overseas, because that's where we have decided to invest. I  cannot give information on the laws on rental properties stateside as they may have a completely different set of regulations. You will have to look at subletting, homeowner association laws, zoning and such. I do know that I have rented from well known online companies (Homeaway, AirBnB,etc)  in which the apartment/condo had written rules for guests that included not speaking to other tenants. At all.  This told me they were not really following tenant regulations about subletting.  They were beautiful, but we had to be were extremely cautious about the volume on the TV and walking "lightly" and if we played music.  I've been in hotels where I can hear other guests put the toilet seat down and open/close drawers,  so I understood that term.  I also lived in a condo in Seattle where the occupants below me were such a nightmare they accused me of being noisy when I was actually sleeping  and complained that my cat was stomping around.   What?   34 years later, that still baffles me! 

We narrowed our list to where we would like to spend more time when we retire.  Someday.  A place with temperate climate all year, where we could drive a short distance and be near everything and where my husband would be able to golf , Also where we could buy a couple of cruising bikes and safely ride them on a beautiful fall or spring afternoon as well as walking the gorgeous seaside paths!   As you get older, you also need to think seriously about health care. Seriously.   One fall could literally bankrupt you if not careful and God forbid you get cancer or some other disease.  We have met many retirees who have moved to South America (Panama, Ecuador, Columbia, Guatemala) because they have some of the best, and least expensive health care in the world.  Spain is in the top 10 for retirement due to the weather and health care.  Another thing to think about is your lifestyle. Can you think about moving far from family and friends?  We found one couple who live in Panama City and actually see their children and grandchildren  more because they are able to fly back to the states every 3 months and stay for several weeks. 

We are not planning on this for several years because we are really a long away from retirement and I am starting a new business,  but we did want to start planning as investment property to have as a hard asset in our portfolio.  We looked at South America and Costa Rica (still thinking about a place in CR) and made a list of pros and cons.  Here are some ideas and you can write yes, no and maybe.
*What are the requirements for Visas:  Work?, Retiree?  Residence?
*Are we able to be away from family and friends for more than a month at a time?
*Would you like to have a place near mountains (skiing), in the city, by the beach or a tropical island type of area with water sports, sand and surf?
Would you like to have a temperate climate, cold weather for winter sports, hot as in the hot and humid tropical weather.
What is your monthly budget? Will it be enough to pay for rent, utilities, insurance, entertainment, restaurants, other?
What does the health care include and what are the ratings?
What can I do in this location as I get older? Can I walk those same stairs, walk those same hills, cook from scratch? Or would I be better off  in my own city with people taking me everywhere and in house/adult home care and having meals delivered?
Will I be able to pick up the foreign language?
How fast can I get home in an emergency? USA to South America: 7 hrs, Europe: 12 hrs, Australia and Asia: 10-14 hrs, Middle East: 16 hrs and even more if you get a discounted fare. These can be up to 32 hours of travel and 3 connections.
Do I like the stores and foods.
Can I get great Internet access?
Is there activities like golf, art, fishing, shopping and other interests?
Are you going to get a work/retiree/residence/working visa?
Do you or can you learn the language?
Do you have animals that will go with you?  Some, like birds and reptiles, may be harder to transport.
Can you live without your hairdresser, nail and brow artist, or other specialists? Or do with who you can find?
Is the area safe?
Can I make friends easily or am I too shy to speak to people I don't know?
If you have small children/young kids, is it an area with good schools, safety, standards and other social aspects?
Can you work when you are there? Will your job transfer you and can you do your job from home overseas?   Is it a viable move when your kids are young  or teens and will it be good for them (emotionally) and for you? IE: no babysitters, no English speaking schools, no after school programs, no gymnastics or dance or cheerleader programs. Will they be able to speak the language and be happy in their new environment?

We went thru this list several times and kept going back to the same place. Spain. Always Spain.  Why?  Because we/guests can drive 5-15 minutes and be near so much shopping, grocery, theatre, local transit, tours, restaurants, golf, beach, mountains and so on. The driving is extremely easy, the roads run east/west/south/north. No twists and turns like Florida or Washington DC.  The other reason?   You can go anywhere in the world from the international airports 45-90 minutes away, to the amazing trains and buses.  In Spain, you are able to fly to anywhere for a day. Lunch in Paris? 1 hour each way. Day in Morocco South Africa is  about 40 minutes each way. Dinner in Rome or Dubrovnik? 1 hour flight each way. We decided that in South America, a day trip would still be in that same country. In Europe, we or our guests could fly in/out of Malaga from anywhere in Europe. Plus we love it.