I see I can purchase X1 Producer from a Sale at Tom Lee Music for only $99. This, on the surface, seems like a good deal considering the original price was $499. 
 I also see the upgrade to X3 is another $200. So that is a total of $300 which I guess is a good deal if X3 is $499 list price. 
Now my question is-- how bad was X1? I tried the demo and didn't really find any new features worth the upgrade from 8.5 to me. And then there seemed to be some issues.  I imagine all the patches fixed the bugs,,?? right? 

It was OK but given the improvements made since, I would skip it and go straight to X3 Producer for $200. No version of SONAR is bug free. I see no value in picking up an old version of SONAR that offers nothing over what you already own, especially if you are also considering getting current.

X3 is turning out to be the most bug free in living memory, well it will be I reckon once the X3D patch comes out (coming soon)... X3C is fine if you disable 64 bit precision engine.
My view is if you are migrating from 8.X jump straight to X3 Pro if it's just an extra $200, definitely worth it and your upgrade path to X4 will be cheaper  (should you decide to take it). Forget about X2/X1 although they were a great three years for me.
 
Cheers :)
 
(post edited - dollar amounts were wrong, See Bobs post)

X3 is my favorite.  I wouldn't bother going to X1 etc., unless it is the cheapest way.  Stable but also is the easiest to adapt to - it is the most thought out system.
 
@

I thought in his post he was saying he could first buy X1 for $99, and then he could upgrade to X3 from X1 for another $199, meaning a total expenditure of around $300.
 
Still X3 is a great release, with TONS of good features and included additional components.
 
Bob Bone

Cakewalk seems to offer the upgrade to X3 Producer for $199 from any Sonar Producer version, if I read it correctly, so if your 8.5.3 is a Producer Edition, that would seem to qualify.
 
(from the Cakewalk site)
 
SONAR X3 Producer Download: Site Price
Upgrade from SONAR X2 Producer $149.00
Upgrade from any SONAR Producer $199.00
Upgrade from any SONAR Studio $299.00
Upgrade from any other SONAR $399.00
Upgrade for any registered customer $449.00
 
Bob Bone
 
 

Ha! Well there is your answer.... say no more (unless you don't have the producer version).

Cactus Music
Now my question is-- how bad was X1? I tried the demo and didn't really find any new features worth the upgrade from 8.5 to me. And then there seemed to be some issues.  I imagine all the patches fixed the bugs,,?? right? 

I recently reinstalled X1 a couple of weeks ago for test.  How bad is it?  Though it's functional, X2 is much better, IMO. But needless to say, I uninstalled it ASAP!  I currently run X2a; I have not taken the plunge for the X3 upgrade...yet.

I didn't see that about "any" version, I sort of assumed they were talking X series, so then that answers it. There is no differance in the upgrade price from X1 or 8.5 so I guess it would be a waste of $99. Thanks. I'll go straight to x4 I think. 

You gotta have Pro though...