IMO that's certainly a better option financially in the long run. But, it appears you want/need something more utilitarian/classic. The spec on an HSE will most certainly have things you don't want/need (22" wheels, climate seats, electric third row etc), so perhaps bridging the gap somehow might suit. What does a SE look like price wise when you configure it? That might be a good compromise/balance.
As with most things in life, unless we are millionaires then the cost will be the primary driving factor, so the discount you get will play a huge part along with residual values. I personally have found that balancing up the following aspects is the best way:
Lowest spend on options
Biggest Discount
Best Residual Value (RV)
Total cost over the term of owning the car (deposit+monthlies+neg equity)
My advice, FWIW, is to spec a S, SE and HSE, plug those three configurations into DTD to see what discount you can get then work out the total cost of the lifetime you expect to own the car. The configurator has a finance option that shows the projected RV's you can use as a yardstick. At the moment after 4 years and 10k miles a year they are:
S - £23,976
SE R-Dynaimc - £26,906
HSE R-Dynamic - £29,111
The overriding problem for you is JLR know that there is a market like yours where you need a half way house, so they are capitalising on this by removing a version where you don't need to add options and/or upselling a higher model.