If you want an Oregon, that's all you'll need. You will need to buy maps for it from Garmin because the 300 does not come with maps. This is a good thing. Garmin's road maps come with a PC program called MapSource included on the DVD with the maps. (You have to buy the version of the maps that come on CD or DVD for the rest of this to work.)
When you install the maps on your PC, you also automatically install the MapSource program. The first thing you need the MapSource program for is to download the maps into the Oregon.
You can set the Oregon up on your dash (either just lay it on the dash or get a proper mount for it) and it will create track files for you as you travel. Any time you wish, you can upload the track files into MapSource and display them on the map. Once the track files are loaded into MapSource you can do a lot of things with them besides display them on the map. There are track tools that let you split and join track files. And you can export the data points from a track file into, say, a spreadsheet if there are other things you want to be able to do for data analysis.
If you have been researching the Oregon, you will probably already know that if you have road maps installed in it, it will allow you to do routing if you need it in a pinch. And it has all the search features you would expect in any good navigation program, eg. for addresses, cities and points of interest (POI) like stores, libraries, parks, burger joints, gas stations, etc. Basically, the Oregon will do everything you can do with a Nuvi but it has a smaller screen and some additional features that are useful for hiking/biking, geocaching and the other sorts of things you do with a handheld.
After using the Oregon for awhile, if you decide you want to have realtime navigation on the laptop I'm pretty sure you can use the Oregon as a USB GPS receiver. I have done that (as well as all the above stuff) with my eTrex Legend HCx and it works really well. Garmin has a free navigation program called nRoute that will work with any maps installed in MapSource on the PC and it will allow you to do realtime navigation with all the usual features.
Just an alternative to think about ... start with the Oregon and expand from there as/when you're ready for whatever you want to do next ... since you sound like you want an Oregon anyway.
...ken...