Sounds like the 27/2910 would be a good fit for your needs. Going from memory, didn't seriously consider any JD products, the 4400 is physically pretty large. Would be concerned about compaction and would check lb/sq. in. on tires (even estimate). I have basically hard sand and the 2710 leaves light prints if it's even a little damp. However, have an area of 'hydric' (sic?) soil, and while it leaves a 3-4" iumpression, it cuts fine (belly) and does not trench. Water pressure pushes it back. Neighbor in his old Duetch left 10" deep puddles.
Sounds like implements are similar as well. Have a 72" deck which goes right through 8" thick grass like butter (cutting 7A). No tiller but I believe the 2710/2910 will take a 5' (4' for sure, and unless you're doing 40A should be fine). Not sure on loader specs--recommend checking for significant difference.
Check a few dealers--prices do vary quite a bit (at least here in MI). Would also do some digging into JD4000 series--have had some significant problems since launched. Check out some Deere specific sites--there are a lot of them. Personally have had some problems with Deere dealers and their corporate--have seen many other posts with similar experiences. Suffice to say their literature is accurate--they stand behind their dealers: No matter how rotten they are. IMO they are just milking a previously good brand name. Appears Kubota is trying for the premium nameplate to replace them. Evident in the couple problem posts I have seen where Kubota bent over backwards and resolved.
Also in dealer attitude and training from my experiences--day and night. But there is always good and bad in all, so make sure you deal with one your comfortable with. Mention this as it seems you think the dealer might be frustrated--if he is, walk. This is huge toy purchase for most (be honest), and taking the time to make sure you get it right is mandatory. Never the slightest pressure from the guy I bought from--when he could have. Endured endless questions and always said he'd get what I wanted when I wanted it.
Good luck.