For dirt work, landscaping, grading etc a track machine is best. Wheeled machines have their place as well though, they are not just a poor mans options. There are applications, like ours, where a wheeled machine excels. Lift and carry type operations, working on concrete all day etc. Places where you need to be able to actually skid, have a good ride and run high speeds without much wear. Track machines are expensive to keep running and wear much faster than wheeled machines. They cost more up front too. IMO you buy a track machine because you need one, not just because you can. If you are doing dirt work you will benefit from one, wheeled machines are not hopeless, they can do some dirt work as well, just not as good and they do not float as nice on soft ground nor do they have the traction. THey do have higher speeds and a smoother ride though, not to mention they can be run in barns and hop curbs all day where a track machine would not be happy.
The issue of vertical versus radial has little to do with overall height. The "reach" people are referring to is the reach forward, not up. Its how far forward the cutting edge of the "standard" bucket would be at whats considered max lift/dump. This measurement is from the forward most part of the machine (tires/tracks generally) to the cutting edge. Its an indication of how well you can reach into the center of a truck or trailer at max height. The "vertical" name comes from the near vertical lift path of those booms. They come forward at first but then lift nearly straight up (like a forklift). Radial machines lift in a radius, meaning they come forward until halfway through the lift path, then they start coming back close to the machine. They will reach further at half height than a vertical but will have less reach at the very top. This is why most large capacity machines are vertical lift paths, it keeps the load closer to the machine and allows for larger capacities. The added complexity of a vertical booms requires strength though and they are often much more bulky than a radial boom leading to obstructions of view and such. Lately the newest machines from all OEMs are getting better though. Its said radial machines can be better for digging as many have greater breakout force. They are better for loading at flatbed height as well due to the further reach at that height. We have both vertical and radial boom machines. We used to always have vertical lift machines but got one radial lift machine because it was small and visibility was good. All of the operators liked it better and for its tasks it does okay, it does not load spreaders as full as the vertical machines, but otherwise works fine for what we ask out of it. Most task are carried out with the boom low anyways. It does not do much reaching. You have to decide what your application will need. My opinion is that if you are in doubt, buy a vertical lift. You will be more upset with the poor reach of a comparable radial lift than you might be with the minor disadvantages of a radial lift. Some radial machines like the Tak have surprisingly high reach specs though. A demo is worth more than specs on paper though, the machine with the most reach on paper is not always that impressive in the real world for some reason, even though the specs are supposedly "standard".
Brand always depends on service. Not relying on your machine for income, and not putting a lot of hours on it means service will be less of a priority for you and opens up your options to buying the machine you like best. If you really will not be piling the hours on like you say, any brand will work. We try to put over 1,000hrs per year on ours and I know many others who do over 3,000hrs per year on their farms. I know a lot of people who don't put 300hrs on their machines in a year also. The fewer hours you put on, the less issues you will generally have. Not needing your machine running nonstop to generate your paycheck allows more flexibility as well. Just because you have that flexibility doesn't mean you want to deal with a junk machine though either. As far as new versus used, you take a big hit on a new machine. Theres a lot of low houred machines out there that would probably be just fine. You can find good deals on lease returns. Make sure you price new ones though so you know if you are actually getting a good deal on a used one or not. All of the new machines now have emissions equipment on them. You'll have to decide if this is something that may bother you or not. Many of the machines larger than 75hp will have DEF if they do not already. Machines smaller than that for the most part do not but some may have any combination of EGR, DOC and DPF The DPF has a very long service interval that you probably wont hit, but with the light use your machine will see make sure you work it hard periodically to keep the DPF from loading up if the machine has one.
As you mentioned, a lot of people have their favorite brands for one reason or another. Some are educated reasons, some are regional reasons, some are personal reasons and others are simply just because. Some have their brands they would consider and some have their brands they would not be caught dead in. Personally the people I listen to and give the most credit to are the ones that have their opinion, but have a good reason why they feel the way they do, and have an open mind about other brands and the other brands advantages. Those who had a bad experience with a brand 5-10 years ago and to this day will not try one doesn't show much of an open mind to me. You can always try a machine, but if things like dealer support matter then there can be issues that may keep someone out of a specific brand for many years. Personally I like the Cat machines and have ran them for a little over two years now. Had a 262C that got traded for a 262C2 and now a 262D, a 242B3 that was traded for a 226B3 and another 242B3 that we still have as well. We trade them around 2k hrs. The B3's are simple and reliable with very nice responsive pilot controls. However they are not comfortable to sit in all day, visibility sucks, working on them is so/so and they lack a lot of the nice improvements of newer series. The original C we had was nice to sit in but the EH controls were poor. Visibility was decent and it was okay to work on for the most part. The C2 didn't really change much but the controls were better, maybe the same update can be made to the older C models as well. The D series doesn't look that much different at first (compared with how different a B and C look) but the more you run them and look at them, the more you notice how much has changed. Almost all of it has changed for the better. Cab is much tighter, cleaner, quieter and more refined slightly. The HVAC freezes you out (never had to run it above level 1 yet). The new display is very nice and allows more customization. The high back, heated, cloth air ride seat is very comfy as are the control pods that move with it. The recline function seems odd in a skid steer, but does allow you to fine tune the position a bit. The lumbar is nice. The seat heater switch location is terrible though. Servicability got better for the most part, but it seems like for every one thing they made nice, another thing went backwards. The new boom lock is nice and can be operated by one person without getting in and out multiple times. Having the air drawn through the rear door keeps everything much cleaner around the motor and under the cab. The A/C condensor stays cleaner and is easier to clean being mounted to the rear door. The nicest change IMO though is under the cab. The HVAC is sealed to the cab, so everything under the cab in front of the drive motors is emptyness. The hydraulic lines in the C series were an abortion. The D series was well thought out, the lines are not all criss crossing and laying down in the slop. The tank sits down in the bottom and the valve bodies all sit up behind the cab out of the slop. Everything is sealed off up front from the rear compartment where the engine is. This keeps the junk out by not creating negative pressure under the cab (I would assume). The new boom allows for much better visibility and the new attachment plate can actually be seen from the cab now. The electric quick attach is slow and worries me though. Electrical components and manure do not mix well, this we learned many years ago on the NH machines with the solenoids mounted to the plate to operate the hydraulic ram. The rear end is much taller than many other machines, but the backup camera can provide the best view of any if you choose to get it.
The machines I like the least are probably the CNH machines. We ran NH machines from the beginning until 2012 and they were great, the most recent series was not though. I think they have fixed a lot of the earlier issues, but the overall design still does not impress me. They have been having a lot of issues at low hours too and just seem very "cheap". Some have had good luck though and some swear by them.
Bobcat makes a great machine and if resale matters they are great on that. They have some things I like and Hate but overall if you just went out an bought one with no research you wouldn't be let down. The Deere machines don't seem too bad to me either. Kubota is really picking up marketshare in the CTL scene. Lots of nice features, and lots of reliable parts. Tak is thought of as the brute force workhorse of CTL's for many people. Terex offers a unique approach also with the ASV machines. JCB/Volvo has their own unique approach as well. Any of these brands will work just fine for you. Go sit in them and drive them around to see which one you like best.
Good luck.
Well, you can cut the bottom of the door off, or remove it, but think of the muddy mess those tracks will dump inside.