I like my spot, it's a former handicap spot (from when this place had unrestricted parking) that has no cars around it and is pretty much right next to to the elevator. This same spot a floor above is actually smaller too, so I think it's the best spot in the building. I could have traded for another, but it still would have required drilling, and the difference between 3 holes and 2 wasn't worth giving this one up
The HOA would have to cover the cost of a new transformer (since it's common infra, unless we did something really weird such as me fronting the cost as a form of a loan to the HOA, which I'm not sure I would want to do anyways), which could be $15k+ all said and done. This would have required budget adjustments (likely with dues increases) and a vote from the residents, which pretty much would have failed by default.
In the future, I expect that there will be a tipping point where we get a bunch of new EV drivers all wanting chargers. At that point, I've offered my assistance to the HOA to plan the project, but if I had to bet it will be a more substantial one-time upgrade (like the aforementioned transformer or using a vendor like EverCharge.
Two additional comments about this.
First -- about switching spaces. Not sure about the OP's situation, but in my condo, the parking spaces are listed on the deed. In my installation, I needed to switch spaces, and was very fortunate to find a space that would work and an owner willing to trade spaces at no cost. She could have said no or made it difficult, but did not. But I did have to pay a lawyer to draft an agreement to swap spaces and then pay for the other owner to hire an attorney to review (and change) the proposed swap agreement.
Second -- I was cautioned early on that obtaining approval of the condo association residents/owners would have been extremely difficult at best and unlikely at worst. Any change that requires the residents to vote also requires a high percentage (75%, I think) of owners to agree, and nothing had ever gotten that high percentage of positive votes in the 20 years or more the association had existed. It wasn't that residents would necessarily vote against, but even getting the 75% to vote at all was difficult. So we carefully avoided any action that required more than Board approval!