As always, buy the newest, best one you can afford because that is always better value and easier than buying the bargain priced one. They're virtually all bargain priced at this point in their cycle. Do not skimp and be prepared to pay a modest premium for the best car.
Totally agree, don't skimp... get the one that you really want even if it's a bit more. Then you won't always be looking for the next one.
I am more convinced than ever that good examples of these cars will hold their own and even appreciate in the long term as long as people continue to cherish things with internal combustion motors.
Would be a great surprise/bonus, but don't buy it for an investment, buy it to use it. I love LOVE the Evora, and it always gets a great reception where ever I bring it, and great conversation at cars & coffee and the like. But when I look at Esprit values, I imagine the same fate for the Evora. Esprit is iconic, fun, and rare (if wikipedia is to be believed, after a 28-year production run only 10,675 Esprits were produced). Yet prices never took off, and have been pretty flat for years. I don't think cost of maintenance is the only factor holding values down - many of it's contemporaries also have eye watering maintenance costs, and have appreciated more. Not sure what it is, the car community loves Lotus, until it's time to pay for one!
If you have the means to get the Evora you want - go for it, enjoy it, become another brand ambassador (you will have to - people will ask you about it). But buy it for now, not what it might be worth later.