Only comment would be to start with manual machines -once you have them mastered, then worry about CNC. I'm only 71 at this point, but I still have a lot of things left to master! Try to find even a HF mini-lathe and mill used, and get started. The sooner you start, the sooner you become experienced, Just a warning though - machining is just as addictive as wood working.
Ok, the leap from $1,000 to $2,500 is a big one. I certainly didn't make it at one time. It took me years. But I know folks that decided they wanted to get into woodworking and dropped at least $2,500 getting themselves outfitted. When you do make the jump, the thought process becomes much less about making sure you can get the job done and becomes more about having quality tools to get the job done.
These YouTube videos provide great woodworking information that contains both traditional and modern methods. Each instructional video contains woodworking how to techniques to improve a woodworkers’ skills and also methods for how to work safe in the shop. If you want entertainment, then watch the video once. If you want learn, watch the again. If you want to master techniques and improve your woodworking skills, watch and study the videos repeatedly.
Maple comes in two varieties: hard and soft. Both varieties are harder than a vast majority of other woods and are moderately priced. Because of their fine, straight grain, both varieties are more stable than many other woods and perfect for tabletops. Exotic varieties of Maple exist – such as Curly, Tiger and Birds-Eye Maple – which are used in fine woodworking for an unparalleled finish, with grain patterns that are extremely unique and distinct but come at a higher cost.
The next important hand tool for the woodworker is an accurate tape measure. Get a retractable one that is at least 25 feet long. Any longer than that, and you start having problems getting it to roll back up. Since measurements on large scale projects can be very susceptible to even the most minute measurement variations, you’ll want to make sure the “hook” or tab at the end of the is firmly attached, with no give. When they get loose, you’ll have as much as 1/8” variation in your measurements. This can add up to some severe accuracy problems in the long run.