I think it's universally agreed that the last DOS versions were considered the best and most stable implementations of the True BASIC environment.
I don't want to bash True BASIC on their official forums (I support the people behind TB fully, I even bought the Gold edition at the old price), but even John Arscott (the most prolific developer using TB that I know), acknowledged the Windows versions had serious issues on the earlier official TB forum.
It depends a bit on what you plan to do with the language, in my opinion. If you really want to create sophisticated GUI applications, you'll surely hit the well known CPU 100% bug, that will probably annoy you. If you mostly do standard BASIC stuff (graphic and text output) and only sometimes use the GUI stuff, you'll generally do fine. Of course being able to create Windows 32-bit EXE files is a plus (that requires Silver) and running programs in a GUI Window has its advantages. I'd also imagine the libraries are better (although judging from the headers, some some look really old, so maybe hardly any changes from the DOS versions!).
I have this Masterminds of Programming book (O'Reilly, 2009, ISBN: 9780596515171), that contains an in-depth interview with Thomas E. Kurtz and he also mentions there that they used to have multiple developers working on the language in the old days and around that time they only had one and that it was difficult to keep developing TB on multiple platforms (probably they offered Windows, classic MacOS 9, they probably already stopped offering Unix versions around that time). So he also seems to acknowledge that they had trouble even back then. This is line in what John Arscott once said, that each new version fixed some bugs and introduced new ones, I assume he mostly meant GUI-related stuff, as I believe the core of the language is generally stable. The company was sold to new owners since, I'm not sure of the current legal status/ownership.
You could consider buying the Bronze version first (6.0 is very much recommended, see below) first. You then get a idea of the language and its limitations. It has some very basic GUI stuff, but it's not documented too well in that version I believe. If you still like what you see, you can then buy the Silver or Gold version and know better what to expect.
I'd recommend to use an open-source editor for editing and then run/compile with TBSYSTEM.EXE separately. I believe this is possible with all offered Windows versions, except Bronze 5.5.
Unfortunately since lowering the prices, there are no upgrade offers anymore. I hope the people behind TB will re-consider this, although, in their defense: the prices have never been this low before.