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Killed my last Craftsmen 42' ( they lasted about 7 yrs each with hubby doing some repairs). looking to get something that is built better and last longer. I am more interested in it being able to carry me(135) and a cart with dirt, rocks, logs, barn cleanout , sometimes up a slope about 30% grade . My old craftsman 2005 could do that , the next one only with running start barely, now....and tranny has died for 2nd time, he replaced oil once that you aren't supposed to be able to do... I use a tow cart and use it as a 'utility vehicle' around my mini farm occasionally. I mow maybe twice a month. I have pasture grasses, not the flattest even terrain. Have used them to hold tension on fence repairs... rocks and roots kill spindles each year. Big deck isn't important to me, as a matter of fact we will have to replace some gates on the divided yards to fit a new mower. (No ZT, hate them) a John Deere 248 was suggested by dealer... Don't think we need the 500-700 series, nor want to spend the $. We have an old Massey Ferguson industrial tractor for grading driveway. We do much of our own maintenance for old folks. There are dealers nearby. Don't need bells and whistles except cup holder...;0)

Thank you for the detailed description in your question. This greatly helps in suggesting a machine for you. Here is my professional diagnosis:
Deere's 100-300 series tractors are classified as 'lawn tractors'. They have light duty transmissions in them that aren't necessarily meant to be used extensively on hills, rough terrain, or towing a substantial amount of weight (anything more than a lawn cart). As you've experienced with your Craftsman, the transmissions just do not hold up longterm in your application. I would expect the same from the transmissions in the Deere 100-300 series.
Which brings me to the 500 series. This series is classified as 'lawn&garden tractor'. These tractors have a medium duty transmission in them with differential lock. These transmissions are designed for hills and medium duty towing (loads a little larger than a cart). At a minimum, this is the series I would professionally suggest to you. I know the sticker price is a bit of a shock, but it sounds like you're tired of dealing with machines that won't take the work load you expect from them.
The 700 series would be the best fit for your situation, in my opinion for a couple of reasons:
1. They are classified as 'garden tractors' and have a heavy duty transmission.
2. The mower decks are drive-over auto-connect, so it is easy to drive off the mower deck when you're not using it. You simply drive onto the deck when you need to mow. These mower decks can also withstand the occasional mowing schedule because they are designed to handle high/thick grass volumes with relative ease.
3. There are 4WD models in this series as well, which will be the best solution for your hills and pulling needs.
4. This machine also has direct shaft drive to the transmission, and the frame will take the rough terrain with ease.

Final thoughts. Matching the correct machine to the job is important both from a productivity standpoint, but also from a financial standpoint. Also, lowers the frustration level and downtime! I know in your original post you weren't looking to spend that kind of money, but if a new one isn't in the budget, I would suggest looking for a good, used one in this series. They used to be the 425, 445 (all 2wd)models, then became the X400(2wd), older X500(4wd), then the X700 series, which is the current series. I hope this gives you some food for thought and answers some questions. Good luck!

Decks size..... and 3000+ or triple that?
Hmmm... cart needs to be able to pull couple hundred on mostly level, maybe half a cart full up a 30% slope (say rocks, logs, water in sprayer)..250lb. JD says it can haul 500-600 in cart ....
Grasses can get 1-2 ft tall between cuttings (once in a while) (yes the Craftsman could do that and discharge. Also used it to chop leaves under the oaks (only started a fire once...lol) had to reverse because mound would get caught, then rechophalf of it....
So, I wanted another 42' deck, was faster, and fit thru my 5 gates, if we go to a 3 blade and larger 48" deck , we will have to replace gates...doable...but I read that 3 blades get bogged down with clippings and can't discharge as well...that could be an issue...also JD decks are 12 or 13 gauge in the 42"... Husquvar are 12 gauge in their 42" ....
Seems 42" deck is only in cheaper lawn tractors...everyone wants bigger ..... Ran into this dilemma before...quality has slipped so that the choice seems to be to buy a 3000 something$ and expect it to last 5-7 years or spend 2-3 times that to last double? We have both Husquvar and JD dealers close by...

I understand about the gates! We have a few of those on our farm as well. For us, we have 2 tractors. A small one for the gated section, and a larger one for the main yard/chores. Getting a tractor with the right transmission in that width can be a challenge. It's going to depend on what your goals are. Either continue with your current path of transmission/machine issues or consider changing some gates. There is nothing better than having the right machine for the job. Just my professional opinion. The final decision is yours, but I hope to have at least given you some food for thought. Good luck!

You need a garden tractor. If buying new that would be the X500 series or the X700 series.
There are also lots of used older machines that are still great. 240, 245, 260, 265, 285, 320, 325, 335, 345, GX series and GT series are all comparable to the X500 series which will include X500, X520, X530, X540, X570, X580, X590 and there are also 4 wheel steer versions with a 4 for the last number (ex. X534) which I'm personally not a fan of.

Then there are the heavy duty garden tractors. 425, 445, 455, X465, X475, X485, X495, X700, X710, X720, X730, X740, X750.
The 4wd versions would be X575, X585, X595, X728, X738, X748, X758.
The 4 wheel steer versions of the X700 series will end with 4. (ex. X734)
All wheel drive with all wheel steer will end with 9. (ex. X739)