Hey Stefan,
So just some thoughts, I was in a similar situation. I had previously done most of the dev work on our Mage 1x store. But I had not had the time/inclination to want to re-learn a lot of things to do the upgrade. I ended up using a previous co-worker to do all the grunt work and get the site up and running on a magento 2.1 base.
The co-worker also had recently moved to magento 2, so he had quite a bit of exp with a 2x site. They also had outsource some of their dev work to a third party company, but he found that this company didnt have much exp on 2x systems, so all the hard work kept getting bounced back to him as the outsourced guy would just screw things up!
4 months later, well i'm much more confident with doing things in the 2.x space for magento. But having someone deal with the initial upgrade gave me some space to take some time getting accustomed with the new landscape.
The main issue I see now, is the lack of decent extensions for certain things, you may have in 1x land. So you need to identify these gaps, and see if the current extension in magento 1x is necessary or it it a nice to have and I can do without it.
I have now found myself writing simple changes and some small customization work. But its not so bad once you get the basics sorted.
Another thing I found was we initially went with a template for the new site, but found the way the template was developed wasnt inline with current magento methods, and this led to js errors. So I ripped the template out and started from fresh, all based on the luma theme.
Anyhow, if you want to touch base and ask any questions about who I used for the upgrade just pm me. I can refer their details they may be able to help out
Regards
Brendan
Developer
