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Assuming it's the big upgrade (eg 1709 to 1803), there's a way to have it use an external drive (or maybe your HDD) instead of freeing up space on your OS drive.
One of my coworkers recently did this to update W10 on a mini-PC with a 32GB SSD.
The really terrible part is that the reason why so many bottom end systems come with only a 32GB eMMC drive (basically a soldered SD card) is that the cheapest OS licensing tier MS offers has among other max system reqs an SSD that small and crappy. Lifting that single req to 64GB would probably eliminate 90% of the not enough disk space pain that Windows Update currently causes.
Did you ever see history portrayed as an old man with a wise brow and pulseless heart, weighing all things in the balance of reason?
Is not rather the genius of history like an eternal, imploring maiden, full of fire, with a burning heart and flaming soul, humanly warm and humanly beautiful?
--Zachris Topelius
Training a telescope on one’s own belly button will only reveal lint. You like that? You go right on staring at it. I prefer looking at galaxies.
-- Sarah Hoyt
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Dropped my phone on a stone floor the other day, so I need to get a new one.
This task seemed easier before I started sifting through existing phones.
Anyway, I have a few dealbreakers. For example, I won't buy a phone that needs a dongle, I want a 3.5 mm headphone jack.
Bluetooth just isn't good enough for any headphones I've tried yet.
Which leads to the next one, a good DAC.
Display size, I'm getting old, I need reading glasses so I need a large screen, but it still needs to fit in my pocket.
Bloatware - I just hate it, I want a clean experience.
OS - I'm using my wife's old iPhone at the moment. FAARRRKKKK!!!!! How can you stand the limitations? It doesn't even have separate volume controls for different playback devices. And if it does I haven't found it.
What are your deal breakers? I thought I'd suggest @chris-maunder this as a weekly poll, but first we need a comprehensive list of deal breakers to start with.
<edit>I don't want recommendations, I'm interested in what criteria you select your phone on</edit>
modified 9-Jun-18 7:12am.
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My wife bought the Samsung A3 some months ago. It is pretty like the S3, but with some limitations that don't bring any problem to her and way cheaper than the S serie. You might get a bigger number if you want a bigger phone.
You might have a look.
M.D.V. 
If something has a solution... Why do we have to worry about?. If it has no solution... For what reason do we have to worry about?
Help me to understand what I'm saying, and I'll explain it better to you
Rating helpful answers is nice, but saying thanks can be even nicer.
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I think I've decided what I want already.
I was more interested in what your deal breakers are.
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missunderstood you. Sorry
M.D.V.
If something has a solution... Why do we have to worry about?. If it has no solution... For what reason do we have to worry about?
Help me to understand what I'm saying, and I'll explain it better to you
Rating helpful answers is nice, but saying thanks can be even nicer.
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Jörgen Andersson wrote: I think I've decided what I want alread
And that would be ... ?
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Probably LG G7 or V30, they come with ESS Sabre ES9218P Quad DAC
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Dealbreakers:
0: Requires special software to manage pictures and music. I should be able to plug a cable into my computer and access my stuff and use explorer.
1: No microSD slot.
2: Cost more than a car payment! 
One more that I don't know exactly how to express, is the hang-up behavior during call waiting. My current phone does not let me hang up on an individual call...it's all or nothing. This means that occasionally I get interrupted by a robo-call but can't hang up without losing the first call. This issue might actually be a carrier issue...not sure. So I guess you're getting the S9?
"Go forth into the source" - Neal Morse
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No, Samsung is loading to much bloat on their phones, or at least used to. I haven't even looked at Samsung to be honest.
There's price too. But that's not a deal breaker for me, though I do buy the cheaper one of two equalish phones.
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It has to fold in half and fit in my shirt pocket. 
"the debugger doesn't tell me anything because this code compiles just fine" - random QA comment
"Facebook is where you tell lies to your friends. Twitter is where you tell the truth to strangers." - chriselst
"I don't drink any more... then again, I don't drink any less." - Mike Mullikins uncle
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Has to talk to my hearing aids. Huh?
If you can keep your head while those about you are losing theirs, perhaps you don't understand the situation.
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I went with cheap, and this seems to be a good deal: https://www.amazon.com/Samsung-Galaxy-Prime-T-Mobile-Black/dp/B0723HG3FG/ref=sr_1_5?rps=1&ie=UTF8&qid=1528513742&sr=8-5&keywords=T-mobile+Samsung+Galaxy+j3+Prime&dpID=41gJlV0wJSL&preST=_SX300_QL70_&dpSrc=srch
Samsung Galaxy J3 Prime T-Mobile (Black) for 139.99. May not be exactly what you are looking for, but the price is right, and if you drop this one, you will not be out so much money. So far working well for me.
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OS update policy; I've so far had a Nexus S, Nexus 5 and Nexus 6P and I appreciate always being on the latest android version.
On the other hand, I have price as a dealbreaker too. So now the Nexus line is replaced with the much more expensive Pixel line, I'm not sure yet what to get when I want a new one.
modified 13-Sep-18 21:01pm.
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My deal-breaker: a 'phone that breaks when I drop it!
More seriously, what with sailing, riding and landscape photography I like a 'Mil-Spec' 'phone. I currently use a Cat S30, and am plotting an upgrade to the S60 when Mrs.LadyWife is not looking. 
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The problem with Bluetooth is that you need high quality headphones. I have the Airpods and I like them: great, clever case sound and no cable mess.
But my Sony MDR-1000X are a hit: full sound and noise reduction. Worth the money!!! 
Press F1 for help or google it.
Greetings from Germany
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Dealbreakers:
- Screen strictly < 5". I need a phone, no tablet.
- < 150€. There is NO reason why a phone should be more expensive than that.
- MicroSD slot AND access to files via simple USB
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Jörgen Andersson wrote: Dropped my phone on a stone floor the other day, so I need to get a new one.
Get a Google Pixel 2 XL just like I did, you know you want too.
It doesn't have 1 and I have no faarrrkkkking idea what number 3 is.
Just buy it.
I have to go now and up vote your post, I think you are the only person on this site who can spell faarrrkkkk.
Michael Martin
Australia
"I controlled my laughter and simple said "No,I am very busy,so I can't write any code for you". The moment they heard this all the smiling face turned into a sad looking face and one of them farted. So I had to leave the place as soon as possible."
- Mr.Prakash One Fine Saturday. 24/04/2004
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I'm currently using a 64gb Xiaomi MiA1. I would buy it again.
My deal breaker is actually community support. I have perfectly good phones that I had to put in the electronics' closet because of obsolete OS versions.
Pros: Android One and a good community support (i.e. custom ROMs when the devices will be unsupported by the manufacturer), cheap (less than 200 EUR), plenty of storage, high audio volume, dual sim/microsd support, headphone jack, bright screen of the right size, battery lasting a couple of days with normal usage (no social network apps). The IR transmitter is also cool (I use it for the projector and air conditioning at the office... coworkers tend to hide their remotes!).
Cons: A bit subpar camera in low light, but there are software fixes for that (GCam thread on XDA). Some carriers with exotic 4G bands are not supported (worth a check before buying). As it's a Chinese phone, there is no manufacturer-provided warranty. USB-C connector so good charging cables are a bit on the expensive side. No user-replaceable battery (but still can be replaced by cheap repair shops).
YMMV
Luca
The Price of Freedom is Eternal Vigilance. -- Wing Commander IV
En Það Besta Sem Guð Hefur Skapað, Er Nýr Dagur.
(But the best thing God has created, is a New Day.)
-- Sigur Ròs - Viðrar vel til loftárása
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I recently bought Xiaomi Mi 8 and it's a great phone. I definitely recommend it.
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Jörgen Andersson wrote: What are your deal breakers?
The name of the phone starts with "i".
The brand of the phone is named after a fruit.
It's currently the most expensive phone on the market, yet it's inferior to cheaper phones.
It comes with iTunes or other malware pre-installed.
Any input or output doesn't adhere to standards such as USB so that you have to buy really expensive proprietary cables (for a phone that is already the most expensive on the market).
It doesn't even have a headphone jack.
It's not new.
I'm really not into second hand stuff.
Things will break sooner or later and when something's already been used chances are it will be sooner rather than later
I've had two Samsung Galaxies now and I'm satisfied with them so my next one will probably be a Galaxy as well (maybe not the newest, but not the cheapest/oldest either)
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[curmudgeon mode]
A part of me just wants a device that is a mobile phone. Doesn't even need an OS or a screen. Give me something with buttons to dial. OK, texting would be an extra, but not necessary - that's what email is for, or just call me. I don't even care if it records messages. If I'm not answering, don't leave a message, I don't care. But in particular, I don't really need all that extra crap - camera, games, FB, LI, etc. It's all fluff that I consumes my time, which, granted, I am in control of and allow it to consume. There's a thing - I really should engage the will forces and change my phone habits. Anyone know of a 12 step program?
[/curmudgeon mode]
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Marc Clifton wrote: Anyone know of a 12 step program?
Sounds like you're doing just fine.
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Deal breakers:
Apple makes it
Battery can't be changed
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