I’m not english speaker, so sorry if you will find mistakes or reading of my text gives you bad emotions
Re#2: The maintenance subscription costs $99 (US) right now, for one year of maintenance and feature updates.
Aaaa, maybe i do not understand correctly? Why you have 99 USD as price?
I have two licenses - One is Standart and one is Pro
For updating of Standart i need to pay 45 USD
For updating of Pro i need to pay 115 USD
Re#3: Yes there is an option to update from Standard to Professional edition. But I won’t recommend Standard for professional use.
Also i’m not fully agree with you that Standart Edition is not a good variant for professional use. Why? -
- It have some benifits that probably worth to mention:
The most useful for me, is that you could receive 2 WM licenses by paying same amount of price as just for purchasing of one Pro license. So generaly you receive 4 machines to activate your licenses.
Maybe it is a bug, or build-in idea that not mentioned on the site, but i figured out this on my own experience. By paying 300 USD, i received 2 activations of Standart, and 2 activations of Pro, and generally pretty happy with it. Some of my friends that did use WM, was pretty sad, when i did explain this “trick”, because they just did pay ones 300 USD for Pro and lost ability to receive 4 licence activations by not paying 300+180=480 (~500 USD)
Lol, i will be sad if after that developer will delete my additional Standart licenses, 
AHAHAHHAHAHAH
Ye, i need to mention that those 2 additional license activations is restricted to features of Standart edition. It is not 4 Pro activations. Just 2 Standart and 2 Pro for amount of money that 2 Pro`s costs.