I am in a similar situation of possibly regretting not buying two right now, but since I don't even have 1 server set up yet, I don't think it will be a huge deal. If I manage to get 1–2 servers set up in the next year, then there is always the chance of buying another license for $199 within that year long period before the price jumps up to $300. Even $99 is a bit much for me to spend at the moment since I just spent $235 on DaVinci Resolve Studio having their first Black Friday sale ever.
I do wish you could use 1 license for 2 PC's though for that $99 price as an incentive for early adopters (since we are not getting cloud based services or whatever else they decide to exclude), but I get that they have to make money somehow.
