You are in a similar situation I was in last year at this exact same time, when I bought my first tractor. I have 13 acres. About 5 of those acres are open/clear/yard areas that are in grass. The other 8 or so acres is woods. I dont do much in the wooded 8 acres aside from cut a little firewood from it, and enjoy walking it and putting walk trails through it. I have 2 horses as well. I wanted a tractor that could move 5' round bales of hay easily, run a 5 to 6 foot rotary cutter if needed, run a box blade, run a disc or roto tiller to put in a garden, and help with tree remove - push tree tops, large limbs into piles, move logs to the wood pile for splitting, etc etc. The tractor I ended up going with was the L2501. In the year I have owned it, it has tackled every job I have tried to accomplish with it. Its small enough that I can put it in the woods and manuever around all the trees, but its not so small that it cant move 1,000-2,000 Lb loads. Im clearing about half to a full acre currently of the wooded area and converting it to more yard space. Ive done it all with this tractor and a chainsaw and a box of matches. Ive cut down large oak trees, go up the tree stim an cut it off where all the branches start, and the little L2501will push these massive tree tops into piles, and then pick up the 10 or 15 foot long stems that and move them to my log pile. Man of these stems are 12-18 inches in diameter. I dont know what a stem that is 10 foot long and 14 inches in diameter weights, but the tractor has moved all of them ive grabbed, and Im moving them with a root rake that weights over 400lbs itself. The L2501 will lift 2,000lbs up off the ground. Its rated at I think 1100 lbs in the spec sheet, but if I remember right that is to lift something up really high. If you are lifting something up just 2 or 3 feet off the ground, as I do with these logs - just enough to move them- Its amazed me what this tractor will pick up. After clearing all the trees and bruning some huge fires of all these tops, I am coming behind it and using my 5' box blade and 72" disc harrow to turn the ground from a mangled wooded mess full of decaying and rotted logs, leaves, and muck into a nice tilled, level powder of dirt which I will soon come back and plant grass seed over. Its a big conversion from heavy woods to this nice cleared smooth ground. Of course the tractor also moves heavy round bales of hay easily. I use a 3pt hitch spike for that, as it was just cheaper than a front end spike, and I only need to move bales around small runs for horses.
I say all that just to give you some insight into how I'm using one of the tractors you are considering. Its been a little work horse for me, and at under $300/month payments. I didn't want a 400 or 500 a month tractor payment. But that was me. I enjoy working in the outdoors and doing these projects but I am a person of many interests and hobbies. I think you have to be realistic about what you want to do with the tractor, then buy what will do the jobs comfortably. I invested a lot of time in watching youtube videos of the various tractors working and what they were capable of, and reading forums and such. I had some folks try to suggest I go bigger, and sure a bigger tractor is nice, but again I didnt want to spend 400++ a month on a tractor payment. My goal was to keep it under 300/month, and I accomplished that.
The best way to approach this in my opinion, if yorue debating between two models, is to simply think of all you want to do, then ask yourself is there is one model that wont do some of it. Or, what do you gain by going bigger on a certain job. For example - both tractors you are looking at will mow 14 acres fine. Both will maintain a driveway fine. So how do you decide? Well how big a mower do you want to mow with? Do you want to go larger than a 60" rotary cutter? if so then you need to go bigger than the L2501. But with that size again is more money, and a bigger trailer to move it. For example - for me, going larger than L2501 made little practical sense. The L2501 will pull and operate implements 60" wide. I have zero need to have anything larger than about 5 foot wide on my property - it would just be more cumbersome to move around and transport. If however these are not limitations for you, and youd prefer to operate implements over 60" wide, then you need to upgrade. If youd rather keep some money in your pocket, and do most of the same work but cut 60" in a pass rather than 72" in a pass, then you can go with the L2501. I dont mind taking an extra few passes to mow something. Having a larger tractor would only save me in time here and there, not in ability for what Im doing on my property.I think thats what you should ask yourself.