I bought my 2012 John Deere 3320 with a cab in July 2012. I now have about 200 hours on it. 10 years previously I had a 1954 Ford NAA. I have a bit of experience with tractors. I have 40 acres at my home and 50 acres at a family hunting cabin to maintain. Most of my work consists of snow plowing, I have a small garden, I use a brush hog to cut tall grass and smaller brush, I've done some food plots, and have cleared some land for new trails in the woods and made a couple of my fields a bit larger. I also do a fair amount of firewood work. As you can see I do a variety of tasks. My 3320 has done all of this well.
My thoughts for tractor size are nothing smaller than 30 - 32 HP at the engine. You want 25 - 30 HP at the PTO. For me a 32 - 40HP tractor is all I could ever need. If you plan on keeping this for many years, when you think you know what you want, think hard about going 1 size bigger. Once you have a tractor you quickly find uses for it you had not previously thought of. It's better to pay a hair more now than realize you have to sell or trade in your tractor because you decided you need a bit more power or you want a factory cab.
As far as attachments they are endless. Make sure you get the skid steer quick attach on your loader. New and used skid steer attachments are everywhere for sale. I find my pallet forks and a good tooth bar for the bucket to be my favorite attachments. I use my forks for carrying brush and logs and helping with my firewood. I probably cut around 10 cords or so a year. I have all sorts of stuff on pallets so I don't have to carry much around anymore. I have a BXpanded Piranha tooth bar and it works great for clearing small trees and brush as well as digging.
As far as tractor features I think the HST transmission is great! I think with this you can get away with a lesser powered tractor for some tasks because you have infinite ground speed capabilities. This can allow you to use a 3 point snow blower, tiller, or brush hog a bit easier on a smaller HP tractor. 1 or 2 extra sets of remote hydraulics for additional attachments in addition to the loader. This can allow you to use a grapple, a hydraulic plow on the loader, and attachments on the back 3 point that may need hydraulic power for tilting or something else. Rear work lights are easy to forget about, but are very handy.
As far as a back hoe, that depends on how much you think it will get used over the long haul. When I was looking around they we're $7,000 - $10,000 range. I figured I could get 1 or 2 summers of decent work out of a back hoe, but after that it would probably sit and take up room. In my opinion back hoes are a bit hard on the tractor itself, especially smaller tractors. They are bulky and get in the way. They are slow to use. Consider what else you could do with this money. You could buy attachemnts, a cab, get a tractor 1 or 2 sizes larger, ect. For me, I put a cab on my tractor which gets used every time I hop in my tractor and living in Northern WI where the winters are long it was a wise move for me. I stay warm on colder days, dry on wet days, I don't get a nose full of dust or allergens, the gnats and mosquitoes can't bit me, and I stay cool on hot days and I don't get sunburned. For the cost of the back hoe and how little I would actually use it over the long haul I could pay someone or rent something to do some digging for me and have change left over.
One thing I have learned and I see differing opinions in this thread, but I think you buy the dealer rather than the tractor. Many of the tractors are good and somewhere in a particular brand you will find a tractor that suits your needs. Dealer support is #1!! My Deere unfortunately turned out to be a lemon! I've had too many problems and they are not getting resolved in a timely fashion. I found out the hard way how important the dealer truly is. If you have a crappy dealer, you will have a crappy tractor if you run into problems. It's not a pleasant experience from my point of view. I know there are many happy Deere owners, unfortunately I am not one of them. I happened to get one of the few lemons off the Deere lot. My 3320 when working properly is a nice tractor. The layout of the controls is pretty good, the loader joystick is very ergonomical. They may have the nicest cab I have personally seen. Don't let my bad experience steer you away from a Deere, but please let it steer you towards a good dealer.
I planned on having this tractor for 20+ years. I am now after 16 months and 200 hours looking at getting rid of it for a Kubota or LS. I priced an LS tractor yesterday. It's a XR4040HC, which is a 40HP with a cab. The cost was $26,500. That is cheap compared to Kubota or Deere. My 32HP cabbed 3320 Deere was $33,000 plus I laid out another $1,200 to add another set of remote hydraulics(3rd SCV). I think an LS will be my next tractor.
Deere and Kubota, maybe several other brands as well hit you in the wallet for all the extras and options. With LS there are very few options because they are mostly already included. You get the skid steer quick attach on the loader with LS. Deere and Kubota this is another $800. LS you get not 1, but 2 extra remote hydraulics(3rd & 4th SCV) included. Deere and Kubota are $1,200 for just the 3rd SCV and I believe another $900 for the 4th. Draft control for the 3 point on the LS is included, Deere and Kubota you pay I believe $400 extra. LS gives you the telescopic stabilizer and draw bar, Deere and Kubota hit you again for the adjustable draw bar. LS also seems to have the longest warranty at 5 years. the 1st 2 years are bumper to bumper, the last 3 years covers the powertrain. The others are 2 - 3 year warranties.
When I was looking for a tractor I looked at John Deere, New Holland, the Kubota
L3400 and
L4600, the Kubota Grand L series, and considered LS. I also looked at Bobcat and Cub Cadet. The Kubota and John Deere were comparable in price and features. I narrowed my list down to Kubota and Deere because of the name, reputation, great dealer financing, and they were in a reasonable distance to my home. LS initially lost out because their lack of dealer financing and my LS dealer at the time was a bit further away than I cared for and he at the time had issues getting tractors in stock. My lesson learned is paying for the name does not always get you quality or support. I see an LS in my near future.
To my surprise I found out many of the compact utility tractors and smaller are not made by the name slapped on the side of the tractor. Kubota is one of the few tractors made by Kubota with their own parts, including the engine. Deere makes most of their tractor with the exception of the drivetrain. It has an Eaton transmission and Yanmar engine which are top of the line names. LS makes tractors for many of the big names. LS makes or has made tractors for New Holland, International, Case, Montana, Farm King, McCormick and a few others. Look at the New Holland Boomer, you can easily see it is an LS but at a much higher price with fewer included options. My guess is LS must be decent if they make tractors for these companies.
Take what you will from this. I'm not trying to necessarily steer you to one brand or another. Take some time and review your options, your present and future needs, and your dealers.