I have a 2009 Simplicity Regent. I'm certainly not a tractor guy, but I have learned a lot about all kinds of different LT's over the last several years. Among the most important thing that I've learned is that nothing combines reliability and cut like a Simplicity. I have absolutely no complaints about this tractor.
The 22HP OHV ELS Briggs engine has been great so far. It is fairly quiet, as quiet as a 22HP engine can be, and is easy to maintain. The oil filter is easily accessible along with the plugs and air filter. I mow a very level .65 acres every 3 days from mid-April through mid-November in the middle of suburbia. In addition, I have pulled carts of mulch and fire wood with ease. Although I certainly wouldn't not do this on a regular basis, the engine doesn't hesitate when pulling the load. Personally, I think it uses more gas than it should, compared to my older 14.5 HP Kohler Command engine in my previous 1999 Craftsman, however, that isn't exactly fair. I estimate I fill up my 5 gallon gas can every 10 hours.
The hanging deck is what sets this tractor a part from the competition. The cut that is produced is second to none. It is perfectly even and striped like a ball park. Gotta love that look! I can remove/install it in 3 minutes or less. That makes maintenance very easy. The only maintenance that I've done is grease the spindles and scrape (and sometimes carefully power wash) underneath every 10 - 14 days. I also bought the mulching kit and Gator Blades. The grass is cut so fine that I can't see any clippings on the lawn. No need for a bagger. However, this is the reason why the deck needs to be cleaned. There are several spots under the deck where grass builds up or simply adheres to the steel. This creates a high rust potential. To combat this, I spray silicone underneath every time I clean it. The deck also has an infinite number of settings in terms of height. I can go as low as 1.5" to as high as 4". I love that I can just turn the handle and adjust the height very easily in any increment I like.
It is a medium duty tractor, comparable to any of the JD X300's. The frame is made of 12 gauge steel, very typical. The tranny is a TT K-46HD. Not sure what the HD means, however, I've done some research and written several emails to TT. As far as I can tell, the HD is simply marketing, it means absolutely nothing. I have read a lot of complaints about the K-46, personally I haven't had any problems with it, however, I only mow and pull a light cart every now and then. I think that if it was pushed to do more ground engaging activities, it would whine. The design of the tractor also enables it to have a tight 14" turning radius. I love that I can cut around all of my flower beds and other obstacles easily.
I love the looks of the tractor. The 20" turf wheels make for a nice look, but are also very functional. Although, because of the turf type design, they tend to spin on wet grass while turning tightly. The 15" front wheels are fine, but tend to wear a bit easily. I have just over 100 hours on them and the tread is a bit worn. I'm told it's typical wear though. The seat is very comfortable and easily adjustable. Combine that with the pivoting front end and the ride is pretty smooth, for a lawn tractor. Finally, Simplicity Orange isn't for everyone, but I personally love it. Can't say the same for my wife.
So, why purchase a Simplicity? Someone purchases a Simplicity if they want a combination of reliability and performance. Remember, the main goal of any lawn tractor is to produce a great looking lawn, and nothing beats a Simplicity at that. Throw in the fact that this tractor should last 20+ years easily, and it is also a great value.