Handling uncertainty of visa expiration date

Many airlines will not permit you to enter CR on anything more than a 90 day ticket, since your visa will be 90 days or less. So, best to purchase tickets that the dates can be changed.
Your required paperwork must be dated less than 6 month old, when it is handed over to immigration.
It will take approx a year possibly more to gain residency after your application.
If you really want to know what the rainy season is rally like, come in Sept,Oct. or November .
July is not very rainy...

I think you can buy an "open ticket" from some airlines, that should solve your problem.  Many people come to Costa Rica to look at real estate and are not sure when they will leave.  As long as you have an open ticket that should work.  If you had a ticket in, and a bus ticket going to Panama for a later date, and then say you will fly out of Panama at a later date, that should also work.  See this video and then talk to Michael and D'Angelo.   https://www.youtube.com/watch?v=ntsHtqU8zuo

You could book a nonrefundable round trip ticket for up to 180 days, and also book a fully refundable round trip ticket to somewhere like Miami or Houston with a date within 90 days of you arrival.  (Verify the selected airline gives full refunds without fees - try United Airlines).  You can then cancel the refundable ticket after getting into Costa Rica.  Then you could make a border run before 90 days and be sure to show your refundable outbound ticket when coming back into Costa Rica.  With that ticket it is likely that they would give you the time until your next flight (if within 90 days).

You could buy a airplane ticket to Bocas del toro, Panama City or Nicaragua.

A couple of things about your plan.  The shortened Visa stamps are generally given to people who are "perpetual tourists" - someone who has not applied for residency and leaves every 90 days because they have to - it really isn't a problem getting a 90 day stamp in your VISA unless you have a record of doing a Visa run every 90 days.  It sounds like you are planning to apply for Residency - and I would suggest that if you are coming in July you should start your application process when you arrive.  The most difficult thing you will have to deal with is opening an account at a Costa Rica bank and setting up the proper deposit schedule.  If you are applying for residency as a Rentista it is a bit more difficult, if you are coming as a Pensionado a little easier. 

As an example of the way things move here in CR, my wife and I applied for our residency (as Rentistas) on a trip here in Nov. of 2013.  We have only THIS MONTH (15 months later) been notified that our application has been approved and we have an appointment on March 26th to pick up our cedulas.  Once your residency application has been submitted, you do not have to leave the country UNLESS you want your U.S. (or whatever country) driver's license to remain valid. 

In Re: your booked return trip (or booked trip out of the country) MUST be within 90 days of your arrival.  Use a fully refundable fare or get a bus ticket from Ticabus.com ($26.00/ person) and dates on these tickets can be changed for up to one year.  If this is your first trip into the country and you have a departure ticket within 90 days of your arrival will pretty much guarantee a 90 day stamp (it is usually only "perpetual tourists" who are given less time).   Once you apply for residency and if you need to keep your Visa valid so you can legally drive you will have no problem with getting a 90 day stamp.  Just show the customs agent your Comprobante (residency application receipt) you will not need to prove you are leaving the country in 90 days and you will get a 90 day stamp.

If you haven't found a lawyer yet, I'd like to suggest Rafael Valverde at www.outlierlegal.com or Roger Peterson at www.plawcr.com.  Both speak excellent English and will take good care of your application.  If you do use one of them please let them know I recommended you. 

As for your paperwork, get everything you can get as soon as possible.  Just remember that all documents must have been issued within six months of your application. Your FBI/Interpol report might be the most difficult thing to get.

Good luck!!

I will add a different opinion. If you have never been here before, I suggest that you wait at least a month or two before you start the residency process.
You do have to continue to leave the country until you have 'received the legal papers saying your application is being considered' and this may take 1 week, a month or even a year after submitting an application.

Kiplarsen, have you already been fingerprinted, signed up with CAJA and had your ID photo taken for your cedula, as your appointment seems a long way off?

*IF* you've never been here before I'd agree with cupa about the residency application but I didn't get that from your post.  I received "the "legal papers saying [my] application [was] being considered" within a week of submitting my application at migración in San Jose where I was fingerprinted, I also supplied photographs to migración - along with a list of all my previous marriages and their dissolution dates, my wife had to do the same thing! jajaja we also had to provide a description of all our tatoos!  lol.  If you decide to apply for residency find a lawyer you can trust right away and work with them through the process it will make things - including opening a bank account - much easier.

Cupa - I received notice of approval of my application only a couple of weeks ago. I am awaiting a copy of my wife's resolution before applying for CAJA.

Hopefully your wife's resolution will be completed by your next appointment, then you will be both be fingerprinted again, photographed again, and after you have provided 'proof' that you are signed up CAJA, will have one last appointment...hopefully... with migration when will be given your cedula. Hurray!!

send me your Skype name. I've been doing this for four years.   [email protected]

@camerawork > why would members send you their contact skype details? Can't you give useful info about the subject on the forum? Thank you.

There is nothing secretive about Skype, nobody can hack you or bother you if they have your Skype address, it's not like giving a telephone number.