What questions to ask when looking for a new API to work with?

Hello,

I work in a small IT department.  We have 5 people on our team.  We have an Oracle database.  We have been developing our web applications in Classic ASP forever (using Dreamweaver). Our company browser is IE10 and Firefox.  We are looking to move forward to a new API (ASP.NET, JAVA, RUBY, PHP, PYTHON, etc.).  We need something that is quick,agile, and preferably free.

What questions should we be asking our selves when looking for a new API and IDE  to work with and move ahead in the future?

Thanks for your input.
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capturetheflagAsked:
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Bob LearnedConnect With a Mentor Commented:
Hmmm...

1) What are your strengths?

2) Do you have the time to learn a new system?

3) How much money do you want to consume making a free tool fit your environment?

4) What kind of training budget do you have?

5) If not free, how high would you be willing to go to purchase a product?

6) Is that product supportable?

7) Is the "community" at large supportive of this product?

(to be continued)
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capturetheflagAuthor Commented:
Thanks for the help.  It's a good start for discussion
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