You ask two interesting questions

As Bichur pointed out, OD+ license is a lifetime one, as in you can keep using the product for as long as you want, but you only get the point updates gratis. There is a bit of controversy there though, because one did get the 1.5 -> 1.9 update at no charge, but in order to obtain a version that has 1.9 bugs fixed one will likely be asked to part company with some greenbacks. At least that's the current policy as per FAQ that Bichur quoted.

As far as the new version is concerned, you are right: the updates have been few and far between. The last non-alpha, non-beta and non-bugfree update escaped Stardock's doors over 2 years ago, April 2007 to be precise. Ever since then a lot of us have been waiting with an empty bowl ala Oliver to not much avail. Island Dog aka Spencer Scott aka Technology Evangelist at Stardock posted here: https://www.wincustomize.com/Articles.aspx?aid=354618 that OD 2.0 is in the works but we know less than nothing about when and how much.

There you go, I hope both of your Qs have now been answered

Yes, sir. All the signs so far indicate towards this being the case. I would love to be proven wrong though because it'd mean that I'd get free bugfixes

With OD+ not being part of Object Desktop, the "12 month" rule does not apply, I believe OD+ pricing structure charges for a new full (1.0, 2.0 etc) version.

A hiccup is that at the time of purchase of 1.9 you do not know when 2.0 will come out so one cannot make an educated decision about whether to purchase now, await until the transition timeframe (period of gratis upgrade) begins or hold off until 2.0 has been released.

 

A lot depends on your OS and the build that you're planning to install. A lot of bugs have been mentioned in threads in the forum so I think it's worth you checking them out.

From personal experience, the amount of bugs was reduced when I moved over from XP to Vista, but the ones that remain are just as bad. My build is OD+ 1.90 (535u) on Vista Business SP2. There is an omnipresent issue with the Weather docklet feed that becomes unavailable and doesn't come back after updating, only restart of OD will bring it back to life. This is the behaviour when using a workaround for the issues that plagued Weather docklet, clearly some still persist. There is an issue with docklets when resuming from Hibernation mode. There is a problem with OD crashing when minimising a window after a fresh OD start. There is an issue with system tray in a tabbed dock sometimes overlaying right-click options of a particular icon. There's a problem of a docklet behaving differently depending on whether it's in a tabbed dock or just a dock. I also have an issue when quite often the recycle bin icon isn't refreshed properly. There's a problem with packaging images because those for system tray are not included. There is a general issue of OD freezing randomly. In addition, rather frequently clicking on an icon doesn't maximise its application to the front, but clicking again minimises it back even though the first part didn't work correctly.

There were more problems on XP, but without having a machine with that OS I can't really speak of them. Make of the above what you will, I certainly hope that SD won't let us down with the next version and I'm sure lots of us are willing to provide bug reports and feedback if given a chance.