i second the Santa Teresa thing its way better than tamarindo. its way more rural and the power can go out at anytime i was there and it would shut down 8 hours a day sometimes didnt really matter though, i went so surf not spend all day on the internet.
I've been a few times. Jaco sucks. It's a fine place to rent a board, get a $15 fish taco, or to get stabbed after dark. Come to think of it, there is a lot of petty crime in Costa Rica. There is a reason that there is a 6' tall chain link and barbed wire fence around EVERYTHING, graveyards, homes, stores, everything. Nothing says "this is a nice safe place" like the armed guards at every ATM and the bars on everyone's windows. Don't take anything out on the beach with you, oh wait, don't leave it in the car because they will break in, oh, and don't leave it in the room because the help can't be trusted. You get one chance to take pictures, because once your fancy DSLR is spotted, you will have a pack of local kids in your shadows waiting to adopt it. Don't drive at night because of all of the drunk drivers. More people die from driving accidents than CANCER in costa rica. Maybe it has something to do with the unpaved roads or the 6 or 8 streetlights in the country. Oh and reptiles. Crocodiles everywhere. Watch out for snakes. I think costa rica prides themselves on the snake population. Like they feed and breed them to be the biggest, nastiest, most aggressive pit vipers on earth. Everywhere you stay has a "grounds keeper", well, that guy's job is 90% killing / trapping snakes and 10% keeping grounds. Scorpions are a nice touch too, they like to hide in your shoes and in the shower. Did someone mention that sh*t hole santa teresa? I went there with my father once and he said that it reminded him of Vietnam, so we had to leave. When someone that fought in 'Nam says something reminds them of 'Nam, that's bad. Dominical and dominicalito were nice. There are good waves in Hermosa but it's the kind of place where the locals burn their trash in the streets and the water quality has been pretty bad thanks to Jaco. Honestly, I would look to the north, or the south, or to carib. All of that said, it's an adventure, so do it and you will have your own stories to tell.
for anyone that cares PERU has 3x as much surf and only shortboards necessary. ying: tons of surf, no crocs/sharx/snakes/scorpions. yang: don't drink the water and crimes of opportunity abound.
Before you leave, decided what type of skill level you and your son have. Do not waste the money going to Witches Rock or Ollies, just go to Playa Colorado's, Nica... instead. Tamarindo is a great little town, with limited surf, but within 5 to 15 minutes drive, there are many excellent breaks. Sandbars to reefs, to rivermouths. Yes there are snakes, crocs, sharks ect, just like Florida or alligators like everywhere else. Jaco is a fun beach break (tide driven), look for trouble and you will fine it. Hermosa will destroy your boards. Best to fly into SJO, depending on where you are coming from... check out "break your Spirit Airlines", for the best deals. Rent a car from Target Car Rental, and head out. Rent a condo thru VRBO or Air BnB. Eat Cheap at the Soda type restaurants. DO NOT DRIVE AT NIGHT! I did once, never again, still shaking in my boots. If you want a good deal and a lot of fun Check out Hacienda Guachipelin near Liberia for a all day rafting, ziplining, horse riding and hot spring. I am taking my 17 year old for his first time in two weeks. One more thing, green season which is now, is much more cost effective. And, yes it will rain, but not all day and mostly at night.