A rabbit hole is a good observation, it's pretty easy to talk yourself (or be talked into) into much more machine and many more implements than you actually will need or regularly use. Keep in mind that after your initial projects are completed the tractor and tooling is something that will probably spend considerable time sitting idle.
As reference I operate a vegetable market garden and small beef cattle operation using several different pieces of equipment. I recently downsized my tractor from an older Farmall 300 to a Kubota L2501 as the Farmall was too large to get enough use here. The L2501 is much better suited to perform the tasks required of a tractor for me. That being said, most everything here is done by using either a BCS two-wheel tractor or a four-wheeler. The L2501 is relegated mostly to FEL work, grading, moving round bales and any jobs requiring a substantial amount of traction (a task the BCS is not good for). The smaller equipment just seems to be more convenient and handier many times than a tractor would be.
From your list of objectives, most of the above projects can be performed using a large lawn & garden tractor and/or an ATV/UTV. If the task required is too large, either break it down further so your available equipment can handle the task, consider rental equipment or just pay someone else to do it. For example, skid logs that are appropriately sized to your machine. If their too large, cut them up further so you can haul them out or cut and split in the woods. With five acres you will run out of property much faster than you think.
As with everything else on forums, my opinion is based off what has worked for me. Your mileage may vary. Personally, I have never understood the need to expend a large capital investment into something that spends much time sitting in the barn. If you can or just want a new toy, then that's another story altogether. Best of luck with whatever you decide on and congratulations on the property. It looks like a great place to live.
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