-Must be a laptop since I don't have place for a desktop setup
-Looking to buy the least expensive option
-I want to do iOS development
-Want to be able to hook up a external monitor later, hence the MBP and not air
-Why new: 3 year old MBP is still over 1000$ and no guarantee
-Biggest concern: new MBP expected in December according to some rumors and I don't want to miss out on new upgrades for the same price and lose some value of the "old" MBP
The current MBP is a very nice machine.
The new MBP is rumored to have some questionable features: Thinner (what will do that do to the keyboard?); touch-sensitive OLED panel replacing real function keys.
I have done a lot of thinking about the whole "when to buy Mac products thing". At first I almost didn't want to buy my first MBP because "what if they announce something new in X weeks/months from now and I miss out!" "What is new announcement in X weeks/months lowers the value of my current MBP!" "Ack I am going to be BEHIND!" These are all real thoughts that I had. Then I realized the flaw in my own logic.
First of all, the value of my MBP is not in its resale value. It's in my ability to complete work for clients which brings me $xxx dollars per hour (or really $xxxxx dollars per week, but that's an entirely different discussion). I have two MBP's in my possession at this very moment that are top of the line and exactly two years apart. If I placed them side by side and told you to pick which one was the newer one, you couldn't. If I let you code on them for one day each and then told you to pick the newer one, you couldn't (unless you looked in "About This Mac" but that would be cheating now, wouldn't it?). Trust me, the hype over the latest and greatest MBP feature is exactly that, marketing hype.
Second, MBP's are honestly just really solid machines for working. The battery life is long, the case is light, the features are more than sufficient for development. My 2+ year old MBP is running like a champ (and if it wasn't I would just take it to Apple, I have Apple Care, and they would fix it). Decide what you are buying the laptop for. If it's for telling your friends that you have the latest and greatest MBP that looks exactly like every other MBP, then wait until the newest one comes out and preorder it, then get ready for it to be old news three weeks later. If you want to build great iOS apps for your own business or for others, then get a good solid machine and start making money with it and stop worrying about all of the Apple hype.
I've decided to wait. The current model will be discounted, and I want to know how many USB-C ports will be on the next version and what the impact will be. I've heard it is painful if not impossible to connect older Cinnema dispays to mac book via USB-C.
Edited to add:
>-I want to do iOS development You can do iOS development on any intel-based mac. My 8 year old mac pro is fine. My Macbook Air is perfectly fine.
>-Want to be able to hook up a external monitor later, >hence the MBP and not air
You can hook up an external monitor to any of the modern macbooks, you just have to purchase an adapter. A mini-display cable will plug into a thunderbolt port, and there are adapters for other cable types (thunderbold to vga, thunderbolt to DVI, etc). I have a set of adapters I carry in a bag just for presentations.
If you want to drive 4k monitors, there be dragons.
The currently available Macbook Pro is very outdated, and is not a good purchase at this time.
Nobody here knows any more about what is coming than such sources. It is up to you to decide how urgently you need an upgrade.
But to answer your question: no, now is not a good time unless you must have one for work. New ones, with what some suspect is a redesign, are just around the corner. Or buy a used one now, wait for the new ones, then turn around and sell the used one for about what you paid for it.
Specific advice : 1 - Don't get this generation macbook air or non retina macbook pro those are just bad value
2 - which ever decision you make,understand that in 6 month you won't care
3 - One way to edge your bets would be buy a used macbook pro now, resell a later when/if you decide to upgrade. Macbook have a great resale value, and by buying used you avoid the biggest part of the asset depreciation which appends in the first couple of years.