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I would point that Dudley Hill (of the first iteration of Pearl Django) played an archtop (an L-5, if I recall correctly), as does current member Tim Lerch. Of course, ears attuned to an absolutely traditional sound might find such a lineup less satisfactory, but I've been listening to Pearl Django for a long, long time and like all their lineups fine. (I particularly enjoy the iterations with David Lange's accordion.)
A segment of this video features Tim on his L-5.
As for a crossover guitar, for a while I had a Michael Dunn petite-bouche with a BigTone, and it fit in quite well with the straight-ahead jazz group I sit in with. I was less happy with its acoustic voice, though that had to do with my preference for grande-bouche sound, such as produced by my preferred Selmer-style, a Dunn Daphne with a B-Band rig--though it is less feedback-resistant than the BigTone guitar was.
My best advice: play as many guitars of all kinds and choose the one that works in the environments you'll be playing in. FWIW, my go-to swing guitar is a 2006 Eastman 805CE, because its acoustic and amplified voices both fall right in the middle of their respective spaces. (As does my unique Tom Crandall archtop, but nobody's going to find another one of those.)
Wow, that Benedetto looks and sounds amazing!! How much did sell for Michael? I have a Benedetto tailpiece on my Cholet - perhaps the closest I'll get to owning a Benedetto!!!
I made a similar decision in the past, I play a lot of solo guitar stuff and gypsy jazz. I got an Eastman and recently "upgraded" to a Selmer Maccaferri Replica by Jean Barault.
My Eastman is very similar to this: https://www.djangobooks.com/Item/eastman-ar810ce
But is mahogany back and sides and an Eastman Kent Armstrong pickup. I used to play it acoustic for gypsy jazz and it has a very large sound as it is a 17" body. With the pickup it has a nice mellow sound to it too, good for solo guitar.
The Jean Barault Selmer Maccaferri Replica is way better for a gypsy jazz sound. It has Brazilian Rosewood back and sides and has a very bright sound. The Eastman with mahogany back and sides has a noticeably more mellow tone.
Looking back I am happy with these guitars and the decisions I made when I got them. The Eastman wasn't perfect for gypsy jazz but was very serviceable and has a big sound. It is great for solo guitar playing and has a nice mellow tone. The Jean Barault Selmer Maccaferri Replica is now perfect for gypsy jazz and really a dream guitar for me.
I'm not sure if I would have been as happy splitting the difference with 2 guitars for different setups.
Some more affordable gypsy guitars like:
https://www.djangobooks.com/Item/eastman-dm1
Hard to say now.
The list prices on those Benedetto Vignola models were in the $18K-$20K range! Only a dozen or so were made so they only show up for sale once every 5 years or more, usually over $10K
Fortunately the Eastman Vignola models are very similar and fill this unique electro/acoustic niche quite well.
@Russell Letson +1 from me for the mention of Dudley Hill. His chord soloing on that archtop (it was indeed an L-5) was part of what gave Pearl Django their unique sound. He befriended me 20+ years ago when I went to my first PJ show and was a true class act. Never forgotten.
If you want to go off the beaten track a little - and bearing in mind you have asked an essentially impossible question - you could have a look at Lava smart guitars. I’ve never played one but Remi Harris has done some videos with his and he gets some good sounds out of it.
Here’s Remi playing his:
There's always at least a few people coming to Django in June, using acoustic archtops and they do just fine in jams.
OP, you need to ask yourself if you're ok with a compromise. Any one guitar to fulfill both worlds, while it will do the job, will be a compromise in some ways. Also I think $1500 for each is enough to buy a couple of good instruments.
Are you truly gigging in a straight ahead jazz setting? Or do you just want to play that style as a hobby? If you are gigging, what is the instrumentation and the repertoire? If it’s just playing around for fun I would get as nice of a gypsy guitar as you can afford, and then get a stimer-style pickup for amplification (which is exactly what I did). If you aren’t in a serious jazz band where you need to “look the part” you can just get a cheap telecaster. A lot of people play jazz on those.
Koran Agan often gigged with his straight ahead jazz trio with his Shopis and a Stimer pickup. For example
If I close my eyes and listen, I'd swear I'm listening to the jazz box and not a Selmer style guitar.
I think members are getting distracted by the title of the post and missing the actual question:
My dilemma is.. can i spend ~$3,000 on a nice jazz guitar for gypsy jazz as well, or can i get away with ~$1,500 for one jazz and one gypsy jazz guitar
This is not a dilemma, it has an obvious answer. I'm sure you will have a better result with ~$1500 each for a jazz guitar and a GJ guitar. You can get perfectly acceptable instruments in that price range, and don't need to compromise on style sound nor your technique.
Anyway, if you decide later you still want to get a really good GJ or jazz guitar, you would be starting at $3k or even more. There is certainly a case of diminishing returns here.