Drop Autodesk subscription plan?

It might work for the 1st two years, though It could be a major pain remembering which features you should use in the newer version to remain compatible with the old. But after two years all bets are off as typically AutoCAD has only allowed saving back so far. For example: A2000i will save to R14, but A2004 won't. And even though A2004 will save to A2000i, you will loose some features (gradient fills for one).
Plan 1: Buy new every 2 years. Year 1: Currently have 2000i, purchase 2004 = $3000 Year 2: Must upgrade 2000i or loose it: = $1200 Year 3: Purchase 2006 (have 2004, 2005) = $3000 Year 4: no cost. Year 5: Must upgrade 2004 = $1200 Year 6: Must upgrade 2005 = $1200 Year 7: Must upgrade 2006 = $1200 etc.
So you end up with a maximum of 3 copies and spend $10,800 total (note that skipping versions does not save money on upgrades anymore.)
Plan 2: Upgrade to 2 copies now, add another in two years and stay on subscription. Year 1: 2000i subscription and purchase 2004 = $3400 Year 2: 2 subscriptions = $800 Year 3: 2 subscriptions and purchase 2004 = $3800 Year 4: 3 subscriptions = $1200 Year 5: 3 subscriptions = $1200 Year 6: 3 subscriptions = $1200 Year 7: 3 subscriptions = $1200 etc.
Total = $12,800 (then 2400 every 2 years) (Note I'm using $400 for both 1 year upgrade and subscription prices and $3000 for new.)
So yes, you do save money the first 4 years ($2000). But after that it costs the same (or more if you miss a required upgrade). And, at least currently you get a discount on keeping your subscription current (ie. it's less than the upgrade price). You might save a bit more if Autocad isn't updated each year, but it looks like they are pretty much on the version per year bandwagon. It gives subscribers something to look forward to, and gives them a feeling the subscription has some value.
Add to that the cost of handleing incompatabilities, loss of productivity because all employees can't use the new enhancements and loss of employee moral (Why do I get stuck with the old version?! syndrome, or the sorry, I can't do that, you'll have to ask Joe, he has the new version syndrome)
Note: skiping every other version use to be common with AutoCAD, but that's when upgrades were a flat price regardless of which version you were upgrading from. Now it's verry much a pay me now or pay me later deal. (And pay me much more if you wait to long)
Just my 2 cents.
-Tim

Also note, once off the subscription plan, if you ever want to get back on it you will have to upgrade all your software to the current version, then pay the subscription price. You pretty much hand back any monitary savings you gained by dropping off the plan. (and possibly more)
-Tim

Ok thanks for your advice Tim.... I will pass it along to my boss.

Hey John,
It sounds like you are considering the economies involved and how to get the biggest bang for your buck. Another thing to consider it to get network licences, especially if you have many casual users (non-full time users).
Just an idea that has helped me keep cost down in the past.
Regards-
SMA