I think taking time to play with it before deciding is smart and helpful even if only to consider new style directions.
So the very first question is , is it great, fab, wearable , versatile( within reason) , had a supporting act or that can be achieved( shoes, topper). Topper is a big issue for md since I run cold, but Ithink you are a better sleeveless- wearer. So for that reason I dont invest in sleeveless items that are at best standing alone, whereas I would do so for the perfect sleeveless item that looks great under several tyoes of jackets.
After that it becomes a very interesting $$ concept which is so personsal and yet conventionslly is skewed in favor of less cost per item. For example, it would not be as noteworthy for someone to show an NAS " haul" of numerous items for same total cost and would be congratulated . But if one has a full wardrobe and could use/enjoy ONE new dress, what is the difference? ( I'm not making a budget limit or value judgement either, just trying to use comparables for purpose of discussing decision- making , so for that, thinking in terms of total budget gives a context).
Even total # of wears comes into play, because I have several dresses I'm not wearing much but if I did, thd more I havd the fewer times I can wear each one so at some point it gets back to, how can I choose items that I will really wear as often as is occasion- appropriate and feel the fabbest in?
Even experimenting can be evaluated in terms of budget. We usually use the adage , well it's an experiment but at least I didn't spend a lot. But maybe that limits us as well and if within budget, what is the difference between a few big experiments or a lot of small ones that still add up?
I do have a fear of wearing a VERY precious item and then ruining it. Not sure where that breakpoint is and I think it would be influenced by the fab- factor. I also am very sensitive about wearing something that could be identified as being very costly, but again, I'm likely doing that at some level already for other budgets, so it's all relative.
I may not be a good fab- magnet because I am not having the experience of trying on lots of divine things that I can't afford. Many things are good but not great, you know? A lot of featured higher- end items even here don't look great on me, so guess I haven't found my drool- worthy brand or maker. I would love to have more " this is the one" experiences to set my bar higher for what is possible in fit and quality.
This is a long ramble, but I thought you raised very interesting considerations and I will enjoy seeing how you work it out.