CF9 to CF2016

For us, code wise cf9-cf11 was no big deal - but we don't use oracle so that is an unknown. We currently have no experience with cf2016 and we are a little hesitant as we have read many threads about issues and we don't like being on the bleeding edge all the time.

Since you admit that you're "not CF experts", I think the best thing you should do is hire a CF expert to perform the installation.  carehart-eiDyI5 (Charlie Arehart) comes to mind.

And I must profess some trepidation at the large number of messages I see in these forums related to upgrading CF by more than one generation.  CF8 to CF11; CF9 to CF2016(CF12); CF7 to CF10.  I know that CF licensing is expensive (one of the reasons why so many are moving away from CF to other things, like .NET), but for every generation skipped when it comes to upgrades, the transition is made just slightly more difficult than it should be, quite often due to deprecated tags/functions, but I see that Java updates are also complicating things.

One solution would be to switch to Lucee.  I'm giving it serious consideration.  Open source.  With support just like you're getting here - forum.

Anyhoo... off my soapbox.

1) Tomcat is required, ever since CF10, because CF is an overlay to a Java-driven server application.  It used to be JRUN, but now it's Tomcat, and without Tomcat there is no ColdFusion.  Period.

2) As far as your second question, that cannot really be answered (accurately) since every environment is different, and every administrator/programmer has different needs/wants.  What do you want to do with it?  It's just one small app, but what does the app do, or need in order to do what it's intended to do?  What do you need?

V/r,

^_^