I really feel the issue with ports is a moot point. We talk about dongles, but we wouldn't need the dongles if we just replace the cable instead. Paying a little more for a proper USB-C cable today will be a better investment than carrying dongles and cribbing about ports any time we get the chance to.
There is just one singular port I miss not having on my MBP 2016, it is HDMI. Coming from a 2011 MBP, seeing as how the new ones were coming with HDMI, I really wanted that. Now, I know I only need a USB-C to HDMI cable instead of an HDMI to HDMI. Still, the whole dongle life thing was all blown too out of proportion, in my opinion. Having 2 ports either side, the ability to charge from any side, is a small little plus that is not appreciated readily till we encounter ourselves falling into the ease of it without even knowing it.
About $2,000. Wait till WWDC, and, if really possible, September. It is just some months more. If you really must have it, then just buy whichever device works for your purpose today, since money saved can be appreciated, but money spent will only depreciate in value. I think, get yourself a spanking new 2017 device this September, and you will also not feel any buyer's remorse.
My 13" 2016 MBP only has 8GB RAM as a flaw against my 2011 15" MBP specced out by me to an SSD and 16GB RAM. But, the new notebook really, truly, kills it in IO. Working on the new machine, it doesn't feel too fast, it feels just right. The only time I get a wow factor is when I transfer stuff here and there. Maybe I have grown accustomed. But, working side by side, I really can see the difference between the old and new. So, save that money for some more months, get a new 2017 device and you will be happy for a far longer time than saving some money and going for 2 year old devices for want of something called ports, the particular problem being easily remedied by using appropriate cables instead of dangling all the dongles. But, the disk IO speeds in the new 2016 notebooks cannot be had in the old, no matter what.