I originally had purchased a 15' Limited (was coming from a 2008 Limited). I went with the Limited because I thought it was a fairly good bang for my buck. I originally wanted an Altitude purely for the aesthetics of the black out parts, but could not bring myself to pay 1-2k less for a vehicle with less options - Thus, the Limited fit my bill. I had a V6 and did some light towing with it (double jet ski trailer and 26 foot boat trailer) and had no issues. I began to buy parts for it to make it look more like an Altitude, which was a fun endeavor and kept me busy but was getting expensive. I also was getting a bit envious of not spending a little bit more and just getting and Overland.
Fast forward 14 months: the lady was out of town and I went down to my dealer to just "look" at the new HA models. Long story short, 48 hours later I had traded in the 15' Limited for a 16' HA V6. KBB and CarMax gave me a fairly close range of the trade in value and the dealer met it. In that 14 months since I had purchased the Limited, with 15k miles, the Limited depreciated ~$13k
Dealer turned around and listed and sold the car for $1k more within a week, so the price variation of their offer to me and their selling point was very close.
As for re-sale value of the HA, I personally can not say. I recall reading here that one person was attempting to trade it in, and it had a similar price drop to the limited (~$12k for 15' or '16), The HA is still a relatively new model though as it was only introduced later in the MY15 life cycle, so detailed info and experience on re-sale value may be limited.
I personally have 0 regrets from moving to the HA:
1) The V6 is nearly the same engine (they did a mild refresh in the '16's). I never had problems towing with the V6. I do miss the pep of the V8 though, but I got over it.
2) The HA will come loaded with many of the features you will have to pay extra for in the Limited (some of which are unavailable on the Limited). The HA came standard with: Tow package, Nav, bi-xeon lights, vented seats (a miracle product for Texas summers), full leather dash, Adaptive cruise control, blind spot warning, folding mirros. In fact, besides the Hemi and HK audio, most everything comes standard.
3) I greatly despise the electronic start/stop that is on all the new '16 models. The Limited you mentioned will have it - take it for a test drive and see if you like it.
4) The HA is technically more suited for off road than a Limited due to the adjustable air suspension. So if that is something to consider- but you would be hard pressed to find many members here who have taken the HA into the deep woods and mud
If off roading is your thing, check out the Overland instead.
5) Aesthetically, I think the HA is just a much better looking car, as it shares the Summit/SRT body work
6) Personally my insurance did go up a little bit more going from the Limited to the HA as it was a newer/pricier car when I first purchased. Just something to consider.
Personally, if they are exactly the same price point I would go with the HA 10 out of 10 times as you just get more bang for the buck in my eyes.