Workflow recommendations?

I can only address one aspect of your question. I shoot 99% with a single device - an SLR... and don't edit on an iPad... however, I think I can offer some advice for using Lightroom (Lr) to organize your images.

Move away from your nested folder structure outside of Lr, and create something similar inside Lr using Collections (you can put Collections inside Lr folders if you like nesting). The 1st advantage you get by doing this is that an image can now appear in multiple Collections without actually being duplicated. And edits made to one image will be reflected in each collection. For example... if an image appears in 3 Collections, and you add a notation to the metadata that it has appeared in Big Dirt and Loud Noise magazine in July 2012, you will see that note regardless of which Collection you are using to look at the image.

I also would also probably recommend using Smart Collections to separate out the different capture devices. In fact, most of your primary Collections might conceivable be Smart Collections. For example - you might set up a Folder (within Lr's Collection panel, not within the OS) for the car event. Inside that Folder you have several Smart Collections that filter on the keyword for the event name, and the dates of the event. (This would common for each Smart Collection) however, within each Smart Collection you add a criteria that filters for each capture device. The advantage to this system is that if you click the arrow next to the enclosing Folder name, you see all images from that event regardless of the device used. Click on the Smart Collections you see just the images from that device.

Once you have one set of Smart Collections set up you can duplicate it them and change only the date filter for each event.

Depending on how you need to find images you can refine these.... but... with Lr you can easily set up a Smart Collections to put all the images you regularly need to find all in one spot. For instance, if you go to the same car event annually the Lr Folder structure may reflect the Date > Event. But you can set up a Smart Collection to also show you all the images from that event regardless of date. Refine that so that only see those images rated 3+ stars. Refine that to only show those images that have been noted as being published.

One of the things you can do with a Lr catalogue is to export a selection of images into a new catalogue. So perhaps you could split off a portion of the catalogue and move it to the iPad. Perhaps just the images from last year's car event? Show the images at this year's event (taking lots of print orders?) plus shoot new images and add these to the catalogue. When you get back home you simply merge the iPad catalogue. I think Carousel is what you are looking for. If not, you may need to bring a laptop with Lr installed.

Anyway... hope this helps....

 

Personally, I like Lr.... but it is a personal choice. Some people don't like the modules in Lr (you have to move from Library to Develop modes in order to edit an image, for instance). I like Lr because - at the moment - I think its image editing tools and RAW conversion is superior. At least for my images. Aperture could very well leap-frog Lr on those aspects with a new release however. Whichever one pick.... just stick with it. Some years the other application will be superior (in reviewer's eyes) and other years your application will be.

You can always set up multiple catalogues in Lr. One for work and one for personal. I tried that for a while, but decided to simply set up two top level folders in my Collections panel.... Work, and --- Family. Even that was more trouble than it's worth... and now I just sort on my projects and names of family members. I ended up having just enough overlap between family and work images that a strict separation was difficult to maintain. I'm a photographer, regardless of where I am.