Well, since you can not have one part OSGi and one part non-OSGi you'll need to make your entire app OSGi. In its simplest form you make a single OSGi bundle out of your entire application. Clearly this is not a best practice but it can be useful to get a feel for deploying a bundle in an OSGi container (Equinox, Felix, Knoplerfish, etc).
To take it to the next level you'll want to start splitting your app into components, components should typically have a set of responsibilities that can be isolated from the rest of your application through a set of interfaces and class dependencies. Identifying these purely by hand can range from rather straightforward for a well designed highly cohesive but loosely coupled application to a nightmare for interlocked source code that you are not familiar with.
Some help can come from tools like JDepend which can show you the coupling of Java packages against other packages/classes in your system. A package with low efferent coupling should be easier to extract into an OSGi bundle than one with high efferent coupling. Even more architectural insight can be had with pro tools like Structure 101.
Purely on a technical level, working daily with an application that consists of 160 OSGi bundles and using Spring DM I can confirm that the transition from "normal" Spring to Spring DM is largely pain free. The extra namespace and the fact that you can (and should) isolate your OSGi specific Spring configuration in separate files makes it even easier to have both with and without OSGi deployment scenarios.
OSGi is a deep and wide component model, documentation I recommend:
- OSGi R4 Specification: Get the PDFs of the Core and Compendium specification, they are canonical, authoritative and very readable. Have a shortcut to them handy at all times, you will consult them.
- Read up on OSGi best practices, there is a large set of things you can do but a somewhat smaller set of things you should do and there are some things you should never do (DynamicImport: * for example).
Some links: