Chippers: Don't know what it's like in your area, but weather has killed about as many oaks and cedars here in the last few years as beetle kill in other areas, and there's a whole bunch of other stuff you don't want (e.g. mesquite). You can end up with a big burn pile just in time for the winds to come up and the burn bans to go into effect. If you have that problem, and own a garden or a foot path or two, I would think a chipper becomes sort of important/useful. Problem with stacking along treelines for the "critter" habitat is that here the critters might not be so desirable - copperheads, bobcats, maybe feral hogs etc. We don't have any quail left in this area, which is what I would prefer to make habitat for. If you like pit vipers, have at it. I don't have a chipper yet, but will probably go for a Woodmaxx within the next couple weeks to I can whittle down this huge burn pile that I never seem to have the right weather conditions or free time to burn. Tractors: I started with a used JD model "A" first and that was a great piece of history to own, then went to another JD because I needed the front end loader and liked green, traded it in on a Kubota in part because the service departments at both JD places near me ____ (fill in the blanks). The upgrade is a more capable machine than the JD model I had before and I was pleasantly surprised to find the loader was equipped with a skid steer type system, which opens up all sorts of rental tool compatibility and special attachment options and you don't have to mess with the archaic JD proprietary system. When I traded up, I got the cab. Here, there are times where I can't really shred consistently perpendicular to the wind and work from downwind to upwind, so on a non-cab version, wearing goggles, earplugs, and a bandana or a Covid mask were at a minimum useful, if not required, pieces of PPE. Now, I get in, shred, get out & don't worry about taking a shower & clogging the drain with dirt/dead grass/weeds. I only have to take care of keeping the tractor breathing. Only issues with a cab are cost & you can't really go under a lot of stuff. Not sure if your place is steep enough to worry about the bit higher CG, but it's something to keep in the back of your mind. Sounds like you're in an area that might be great weather year round so you've always got growth on the property and not so much potential drought problems and oppressive heat & humidity, so maybe a cab is not appropriate for your area. On zero turns: I have one for the places the tractor can't go and I need the PPE for it. I know a guy that has a 60" Kubota with the hydraulic deck lift and a Kubota branded engine who mows a lot of acres with it and swears by it. It's a nice machine, but I wouldn't buy it instead of a tractor unless all you want to do is mow or pull something behind it that doesn't weigh much (e.g. you don't think you'd ever really use loader arms enough to make it worth it). Those big Kubota zero turns come fully equipped with sticker shock, so there is that. You can buy a small Kubota tractor for almost the same price as a big Kubota zero turn if you're not careful. If you can get within 42"-48" of borders with your tractor, Kubota has small zero turns (a 42 & a 48) that are fairly priced and Stihl has come out with a line of zero turns including a 42 and they might be a bit cheaper than Kubota. I saw somewhere the Stihls are being made by Ferris, but I don't know if that's true.