it really depends on how much resale value plays a part in one's decision making process. some will find appreciation in the watch most and forgo value. others will put value first, then forgo the design/features.
I used to recommend to all first timers a rollie or a speedy blindly. But I see now that it was not really good advice.
Now I say recommend to
buy watch that you truly appreciate and can afford, with the intention to keep it forever.
After decades you will look back and that first hard earned hard thought watch will remind you about the time and how you bought that watch.
if you bought a watch that you can afford, there won't be any regrets (since all luxuries lose money anyway), but a lot of sentimental value for a particular time in your life.
maybe its just me, there's financial worries anywhere, I'd like my hobby to be free from it.
that said, the best value in luxury items is in the used market. and i am shameless when it comes to buying pre-owned.