You're very welcome! I'm glad it worked out, at least for now.
Although using Tracker and Combat Reporter in a multi-monitor setup is ideal, it is certainly feasible to use them on a single monitor setup, even on a 15" screen. Start Tracker, Combat Reporter, and the game, then use the Alt+Tab key combination (I believe this is Command + Tab on a Mac keyboard) to allow you to switch between them. That's a benefit of running the game in windowed mode - the ability to switch between multiple programs much more gracefully than would be possible if the game were running in full screen mode. One program will be visible 'on top' at any given time while the others are open in the background.
There is a bit of work involved in setting up both WitP Tracker and Combat Reporter, but they are easy to use after that. It is a common opinion around these forums that once you use them, they become indispensable tools for playing the game. Most, if not all, of the information both programs provide is already available in the game - their utility is derived from how they organize that information. Information management is as integral to WitP as logistics is to war. Combat Reporter is the 'tactical' tool to help one get through each turn efficiently whereas Tracker is the 'strategic' tool to help one delve deeper into the data for long-term decision making. For one brief example, Combat Reporter shows you all the sighting reports for a given turn and then graphically pinpoints the location of each on a game map displayed on the bottom half of the Combat Reporter window. As you can imagine, this is a really useful way of organizing the coordinate information the game gives you.
As an alternative, keep in mind that it is possible to run multiple monitor setups from some laptops. I've never owned one, but Macbook Pros tend to be quite capable laptops - I'd be surprised if yours couldn't do this. So, it's quite possible that you don't *have* to wait for your next computer in order to use multiple monitors.
The generation of Macbook Pro that you have will determine what type of video connection(s) are used and possibly how many monitors can be connected at once, but I would bet that at least one secondary monitor could be added without too much hassle. This setup could be as simple as plugging a second monitor into the Macbook's video port (for instance, later generations of Macbooks would be using a Display Port). If you really want to go all-out, you could potentially build a complete 'workstation' setup complete with multiple desktop monitors, external keyboard, and mouse. This latter setup would give you a full desktop user experience when at your desk, and you could still use the Alt+Tab feature when using only the Macbook screen on the road.
Finally, keep in mind that the resolution of a monitor is the actual screen 'real-estate' - not the physical dimensions of the monitor. The physical dimensions of the monitor determine how 'big' (or 'small') the graphics and text appear on the screen for a given resolution. As an extreme example, it's certainly possible to run a 4k resolution on a 15" screen given that the screen and video card are both capable of that resolution - but you'd need really good eyesight to be able to read anything on it. At the other end of the spectrum, this is why TVs are typically much less expensive than computer monitors - even though the TVs are physically much larger. A 60" 1080p TV is running the same resolution as the typical 24" computer monitor.
I've rambled enough for one post, but I'd be happy to help if you'd like to know more.