Well the first thing you do is call your reseller. It is not hard but you have to know what you are doing. They go to class to get certified in it so there are no issues. If you do a "ride along" with your reseller the first time you can generally learn how to do the future ones on your own.

We have done upgrades before without issues.  We've had Sage for years.  But we've never done one in conjunction with a major server upgrade at the same time.

If you have done parallel upgrades before then what's the issue?  

We have never skipped this many generations before.  And we have never upgraded a server at the same time.  Thought there might be some nuances.

4.4 to 2014 is no huge deal in the situation you outline.

You will have to re do A/P check formats or you will have some issues however.   I usually do it from scratch.  Some hunt through and find the formulas that need to be changed.

I do recommend a test upgrade however.

To expand on what my  esteemed colleague has posted. You have to do a parallel upgrade which allows you to install and test on the new server while people are still working on the older server. You can migrate data, convert data, setup new forms all the while people work away on the old server. When you have everything worked out all you have to do is convert the live data, run work station setup and go live without a hitch. Note that you would want to make a copy of the live company and migrate over this copy and test.

"Esteemed colleague"?    Wow.   Thank you  BL.

Just to clarify for others who might read these posts.  If you have done upgrades before and generally understand the process,   the 4.4 to 2014 isn't anything overly complicated.

Now if you have never done an upgrade before it can be a bit more complicated to gain the base knowledge.   I don't want to belittle anyone's knowledge gained from prior experience especially "the wizard" BL.  :).  

"Esteemed colleague"?    Wow.   Thank you  BL.

Just to clarify for others who might read these posts.  If you have done upgrades before and generally understand the process,   the 4.4 to 2014 isn't anything overly complicated.

Now if you have never done an upgrade before it can be a bit more complicated to gain the base knowledge.   I don't want to belittle anyone's knowledge gained from prior experience especially "the wizard" BL.  :).  

Last night, we did the upgrade and migration.

We appreciate all of the suggestions and help that allowed us to make it through.

We're using the new version today while continuing to modify our forms.