I recently purchased the FCS baseball style cap in black which is currently available on amazon: https://www.amazon.com/FCS-Essential-Surf-Hat-Light/dp/B084YH67B5/ref=sr_1_3?dchild=1&qid=1603826452&refinements=p_4%3AFCS&s=apparel&sr=1-3
I liked the look of the bucket hat, but I have long hair and I figured I might as well use my pony tail or braid as leverage to keep the cap on. Also, I realized that baseball-style caps have the advantage of having a brim that can catch water on only one side. It got pushed over my head onto my shoulders about 50% of the time that I had to dive under a wave (due to water pushing against brim) and managed to stay in place during every wipeout where most of the water volume was hitting me from behind. I imagine that a bucket style hat is probably more prone to get pushed forward as well as backwards because it has a 360 brim.
Regardless, even when it did get pushed back while duck-diving I never lost the cap because of the chin-strap and it was easy to just pull back on. For safe keeping I also liked that I could attach the long cord to my bikini strap under my wetsuit, but thus far I've not needed that backup with the secure chin strap. Also, if you're concerned at all about looking goofy, I was told by a friend that from a distance the cap just looked like a wetsuit hood, so now I don't feel self conscious at all wearing it.
A lot of car makes have keyless code pads that you can install. They make life really easy for surfing. Just hide your keys in your car, lock it, and be on your way.
Note: I am not endorsing the above-linked product. (I’ve never used it; my car has a factory installed key pad). The link is for illustration only of what I’m talking about. That being said, it may be amazing- I have no idea since I haven’t used it. Do your own research before purchasing.
So, to me the first one looks kind of thin and maybe more like a gun? But I am also a beginner so I'm not completely sure. #3 looks the most like what you might want to me. If you can get the volume of the first board maybe do that to help gauge if it's good for you. I found this https://www.facebook.com/marketplace/item/600581733959468/ Post and the middle board is the kind of shape/type of board I think you should look for. I found this post https://www.facebook.com/marketplace/item/330968054947581/ as well and I would say these are what you want but idk they r expensive.
I surf obsf frequently, and I run a 4/3 with booties and a hood. The arm workout you get from paddling through rip currents and getting caught inside is normally enough to keep me warm while I’m surfing, but I always keep a hot water jug in my car so I can warm up and get any extra sand off of my wetsuit. It’s a 2.5 gal jug with a neoprene sleeve to keep the water hot. I bought mine from my local shop for around $30. I found this one on Amazon, but I would head to you local shop and pick one up. https://www.amazon.com/Better-Surf-than-Sorry-Shower/dp/B084NY12WG
to echo the other commenter, you can get a roof rack setup, and that has pads and straps. You could also DIY with like... pool noodles and ratchet straps.
I got this setup off amazon. Seems to work well, but I only use it around town, haven't tested it at highway speeds
Can snag a Casio on amazing for like 12 bucks and they last forever. Even if it lasts you a year it’s a cheap easily replaceable watch. My go to surf watch.
I personally have a Thule 810:https://www.amazon.com/gp/product/B004OTZ6F2/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1
Not sure how "affordable" it is, but has been fine for me the 4yrs I've owned it. I've transported both paddle & surf up to 2 stacked as far as a few hundred miles at a time.
What makes you think you'll have to ditch the skateboard in a few months? I'm not sure if it holds true for surf-skates as much as other skateboards, but ~100 is roughly where you start getting into the "Actually quality for your money" range when it comes to short/longboards.
Regarding the board size difference of the two options, that is going to mostly impact your turning radius and be roughly analogous to a shorter board vs a longer board in surfing.
That being said, looking at the boards you're talking about I'm not sure how well they'll actually work to help with your surfing skills. Most Surf-Skate boards have a specially designed truck system that allows you to pump as well as carve as if you were on a wave. The Street-Surfing set up looks like they just bought a bunch of furniture casters from a home improvement store and threw those on the front. From a skating perspective, this will likely lead to some frustration with balance because it opens the opportunity for digging your nose rail into the ground while trying to turn if your weight happens to be off.
I think if you go with a more traditional longboard, or a longboard with trucks like above, you'll get a much better result. A lot of the skate parks around the island are bowl-heavy, so you can use them for carving practice real easy. Also depending on where you're looking to practice, Honolulu County has some dumb laws about skating. Illegal in the street on the whole island (sidewalk only) and completely illegal in the Waikiki District.