First of all, If you're a registered iOS Dev, you should have access to the WWDC 2010 Sessions. One of those sessions covered a bit of what you're talking about: "Session 117, Building a Server-driven User Experience". You should be able to find it on iTunes.
A smart combination of REST / JSON / Core Data works like a charm and is a huge time-saver if you plan to reuse your code, but will require knowledge about HTTP (and knowledge about Core Data, if you want your apps to perform well and safe).
So the key is to understand REST and Core Data.
Understanding REST means Understanding HTTP Methods (GET, POST, PUT, DELETE, ...HEAD ?) and Response-Codes (2xx, 3xx, 4xx, 5xx) and Headers (Last-Modified, If-Modified-Since, Etag, ...)
Understanding Core Data means knowing how to design your Model, setting up relations, handling time-consuming operations (deletes, inserts, updates), and how to make things happen in the background so your UI keeps responsive. And of course how to query locally on sqlite (eg. for prefetching id's so you can update objects instead of create new ones once you get their server-side equivalents).
If you plan to implement a reusable API for the tasks you mentioned, you should make sure you understand REST and Core Data, because that's where you will probably do the most coding. (Existing API's - ASIHttpRequest for the network layer (or any other) and any good JSON lib (eg. SBJSON) for parsing will do the job.
The key to make such an API simple is to have your server provide a RESTful Service, and your Entities holding the required attributes (dateCreated, dateLastModified, etc.) so you can create Requests (easily done with ASIHttpRequest, be they GET, PUT, POST, DELETE) and add the appropriate Http-Headers, e.g. for a Conditional GET: If-Modified-Since.
If you already feel comfortable with Core Data and can handle JSON and can easily do HTTP Request and handle Responses (again, ASIHttpRequest helps a lot here, but there are others, or you can stick to the lower-level Apple NS-Classes and do it yourself), then all you need is to set the correct HTTP Headers for your Requests, and handle the Http-Response-Codes appropriately (assuming your Server is REST-ful).
If your primary goal is to avoid to re-update a Core-Data entity from a server-side equivalent, just make sure you have a "last-modified" attribute in your entity, and do a conditional GET to the server (setting the "If-Modified-Since" Http-Header to your entities "last-modified" date. The server will respond with Status-Code 304 (Not-Modified) if that resource didn't change (assuming the server is REST-ful). If it changed, the server will set the "Last-Modified" Http-Header to the date the last change was made, will respond with Status-Code 200 and deliver the resource in the body (eg. in JSON format).
So, as always, the answer is to your question is as always probably 'it depends'.
It mostly depends what you'd like to put in your reusable do-it-all core-data/rest layer.
To tell you numbers: It took me 6 months (in my spare time, at a pace of 3-10 hours per week) to have mine where I wanted it to be, and honestly I'm still refactoring, renaming, to let it handle special use-cases (cancellation of requests, roll-backs etc) and provide fine-grained call-backs (reachability, network-layer, serialization, core data saving...), . But it's pretty clean and elaborate and optimized and hopefully fits my employer's general needs (an online market-place for classifieds with multiple iOS apps). That time included doing learning, testing, optimizing, debugging and constantly changing my API (First adding functionality, then improving it, then radically simplifying it, and debugging it again).
If time-to-market is your priority, you're better off with a simple and pragmatic approach: Nevermind reusability, just keep the learnings in mind, and refactor in the next project, reusing and fixing code here and there. In the end, the sum of all experiences might materialize in a clear vision of HOW your API works and WHAT it provides. If you're not there yet, keep your hands of trying to make it part of project budget, and just try to reuse as much of stable 3'rd-Party API's out there.
Sorry for the lenghty response, I felt you were stepping into something like building a generic API or even framework. Those things take time, knowledge, housekeeping and long-term commitment, and most of the time, they are a waste of time, because you never finish them.
If you just want to handle specific caching scenarios to allow offline usage of your app and minimize network traffic, then you can of course just implement those features. Just set if-modified-since headers in your request, inspect last-modified headers or etags, and keep that info persistent in your persistet entities so you can resubmit this info in later requests. Of course I'd also recommend caching (persistently) resources such as images locally, using the same HTTP headers.
If you have the luxury of modifying (in a REST-ful manner) the server-side service, then you're fine, provided you implement it well (from experience, you can save as much as 3/4 of network/parsing code iOS-side if the service behaves well (returns appropriate HTTP status codes, avoids checks for nil, number transformations from strings, dates, provide lookup-id's instead of implicit strings etc...).
If you don't have that luxury, then either that service is at least REST-ful (which helps a lot), or you'll have to fix things client-side (which is a pain, often).
