Why is the carbonyl IR frequency for a carboxylic acid lower than that of a ketone whilst an ester is higher than a ketone
First things first, it's important to realise that functional groups may have IR frequencies over quite a broad range. I've provided the table below, from which you can see that actually there is a great deal of overlap depending upon the actual 'environment' of the functional group in question. Ketones and acids, for example, cover a very similar portion of the spectrum.


  Stretching frequencies of common carbonyl groups (Taken from Introduction to Spectroscopy, Pavia and Lampman. 
  


That said, the difference between the frequency range of an acid vs an ester is an interesting one, as on the surface of it they are electronically quite similar (in both cases the carbonyl is next to an electronegative oxygen). 


  @RobChem: This would seem to suggest that the acid decreases the carbonyl bond strength and the ester weakens it. This must be as a result of the fact that in the ester inductive withdrawal is more effective than resonance and the converse is true in the acid.


In your statement, you may have gotten a little confused, remember that the stretching frequency increases with bond strength. Therefore using your data we can say that the ester is stronger than the ketone whilst the acid is weaker. 

We can explain the ester being stronger by considering the effect of the electronegative oxygen withdrawing electron density:


  


This argument however, fails to explain why the carboxylic acid has a stretching frequency below that of the ketone, since, as was already said, they both have the oxygen adjacent to the carbonyl. 

One rationalisation for this is that the carboxylic acid group doesn't exist in isolation but rather interacts with other carboxylic acids in a hydrogen bonding interaction, which weakens the C=O bond: 


  


This hydrogen bonding concept is universal, for instance in methyl salicylate, the C=O bond has dropped to well below that expected for an ester: