giving Sonar users an opportunity to jump in on these current deals, would it be a bad idea to just sit out and get a DAW later down the line?
 
I don't want to miss out on a "exceptionally" good deal (something that may not happen later), but at the same time I'm planning on using Sonar as long as possible.
 
On the fence here....

It's a tricky one.....
Sonar could potentially carry on working for years
 
Then again it might not so taking a good deal now might be a shrewd move. Or end up paying a lot more sooner than you think. Swings and roundabouts.
 
I can't decide either!

I plan to use SONAR as long as possible, too.  But in the event I'll need to move on someday, I'm learning Reaper in my spare time. No surprises, no stress if/when the time comes.

I wouldn't worry too much. While a number of the specific deal will probably never return, deals nearly as good will likely happen this time of year again. I mean Studio One was not much cheaper with the Sonar crossgrade than just getting it from some place like Audiodeluxe on the black Friday sale. The only deal that might be something of a "one time only" is Cubase, it rarely seems to go on sale.
 
However that said you could look at just jumping on a new DAW. I did because I figure while Sonar won't break, I can probably make it run for the next 20 years, I'd rather just start learning something new and getting used to the new workflow.
 
I picked up Cubase, personally, and I quite like it.

Tough call Meshers. Totally personal call too.
 
Is what I'm doing (or have done) what you need to do? Probably not.

It's a tough call.
On one hand, Sonar hasn't stopped working.
On the other, it's prudent to at least investigate the options... knowing that (to remain current) you'll ultimately have to make a move.  (This assumes Cakewalk doesn't get sold/resurrected)
 
There are some great deals available right now.
If you've got the budget, it's not a bad thing to have a couple different options in the toolbox.
 

FWIW, I already have several other DAW applications in my toolbox.
Even so, I'm not sure which will replace Sonar as my primary DAW application.  
There are compromises no matter which you choose...
 
ie: Samplitude might seem an obvious choice for me (extensive background with it in the past - wrote an English user's manual for Samplitude 2496)... but it lacks Track Templates. 
Small but extremely useful/powerful feature...
Can I live without Track Templates? yes
Do I want to live without Track Templates?  NO! 
 

Sycraft
However that said you could look at just jumping on a new DAW. I did because I figure while Sonar won't break, I can probably make it run for the next 20 years, I'd rather just start learning something new and getting used to the new workflow.

Unfortunately, there's nothing to guarantee that a new daw we switch to won't also go out of business.
My confidence and feeling of security have taken a hit.

I have licenses for Studio One Pro 3, Reaper 5 and Mixbus32C.
 
One of those has go to live longer than me, right?
 
BTW, I'm almost 65 if that makes any difference.

The one downside
 
to Reaper is
 
their tutorials.
 
You have to
 
listen to
 
Kenny Gioia
 
talk like
 
this.