So, you're a hobbyist. How many goes does it take to get a functional project?
Usually one. I don't make PCBs, so I almost always work on the same prototype until it is finished. That prototype is then also the "completed product". So that's very cost-effective, if you like.
Sometimes however you build a prototype and you'll measure and test stuff and you'll notice that it's just the completely wrong direction. Then the prototype goes into the bin and you start over.
Obviously that's a 'depends' sort of question, but I feel like I'm probably too worried about making mistakes. How many bucks worth of parts do you write off on prototypes?
Well, that depends. Small stuff (resistors, small caps etc.) goes into the bin when removed from a prototype. Sometimes I'll blow something up, but that's somewhat rare. The most expensive parts in a project are usually those that you won't blow up anyway. Stuff like cases, connectors, transformers, ...
OTOH integrated power ICs can be somewhat expensive (couple bucks to 10, 20, 30, 50 €) and you may blow them up, especially when supplied with high power with no preceding testing done. Rule of thumb: If that part costs more than 5 € or so and/or has a lot of pins, you wanna make sure you don't blow it up. Or you avoid them in the first place, because they often have few advantages for a hobbyist.
A related question might be, how many prototypes work first time?
Well, that a prototype just works fine out of the box happens, but not for more complicated circuits. Although that happens, too.