I live in NJ in a wooded area with 2.3 acres. I grew up on a dirt road in NH back in the 60's on a gentleman's farm. My dad was a master machinest and yet we always had some beef cattle, an occasional pig, we burned 12 cord of wood each winter in a Sam Daniels furnace which was in the basement of a 200 y/o house and we made maple syrup every March sometimes up to 100 gallons a season and burned an additional 12 cord of wood in about a months time making the syrup. We hayed in the spring/summer/fall and when I was old enough to drive my dad had bought an old used IH 330 utility with a FEL. Prior to that he had MF 30 and a 35 industrial with an FEL and a BH. He had several heart atacks and had to sell the MF 35. I loved that tractor and he had bought it new. They were all collar shift transmissions. The IH had a torque converter which I would use on an occasion but pretty much stuck to the standard gears.
About 10 years ago now I purchased a used 2005, JD 990 (collar shift, 3 FW, 1 R with 3 ranges giving 9 fw and 3 r) with a 300CX FEL and an 8B BH. It had only 75 hours on it. I have used it for all kinds of things for myself and neighbors and I have added a lot of things to it with a whole lot more that I want to do as well. I love the tractor. It has 40 hp and it is a MFWD. I wouldn't want anything smaller. I would love to have more lift power on the FEL and even more power in the BH. I have some times been tempted to look at something else but I always come back to the points that it is a simple tractor like what I grew up with. There are no electronics on it. It is a complete Yanmar JD tractor. It runs like a top and it is easy to service. When I am doing a lot of FEL work I could wish it was a shuttle shift transmission with 12 FW and 12 R but it isn't. It is built like a tank. I also would not want a HST drive. I have tried them before and yes they have their advantages but what happens when you run into a problem with them.
This is just one more perspective for your intake. I am in my 62nd year now. I still have a lot of things that I want to do with the 990. I am just too busy at my work with everything. That is what happens when you have to run a company. But there are times I am happy to just get on the tractor and work. The 990 has paid for itself over and over again. I have seen prices on it now where I could sell it for more than I paid for it so it has been a great investment. I hope this gives you a little more input to help you in your decision making process. See some pics below. The first two are when I got my PTO
chipper and my winch.