Can I reply your question with another question?
What do you miss the most on android? Because I am seriously thinking of jumping, but I live in Brazil and cellphones here are REALLY expensive. Right now, I have a 640 XL, looking forward for the 950 XL which still doesn't sell around here. I'm also a carrier client for a very long time, which usually means huge discounts. Right now I could upgrade to a G4 (which I'm inclined not to because I'm a large screen guy) or a Note Edge (which I'm inclined not to because it's very dated and probably won't get 6.0 or 7.0 features) which price around the same with my carrier discount.
When I studied the possibility of a switch, there were a few major holdbacks:
-I really like the jumplist feautre in W10M. Makes thing easier to track down on just about any app. I find Android quite messy whenever I'm trying to find anything. Nothings is alfabetically organized, settings change name every other phone and I usually have the hardest of times trying to find just about anything in an android phone. I know that I'll get used to it, but having a steep learning curve makes a platform unapealling for me.
I personally didn't find the learning curve all that steep. No worse than learning anything else new and in general, you don't need to go into setttings that often to really worry about it. As for the listing of apps, you can typically put them in alphabetical order or search for them or in order of most used.
-I'm really into the skype+messaging integration. I love interactive notifications and I know they don't work like that on Android
The Skype-IM integration is new so probably why it hasn't made it to Android as of yet. I'm assuming it will eventually make it's way over as it's easy to do things like that on Android. Currently there's Hangouts integration but if you don't use that then it's rather pointless. Android has interactive notifications...
-I have an 50GB+ music collection on my OneDrive I stream via Groove. Streaming services don't have all the music I listen to (Yes, I'm that alternative), so having my music collection in Onedrive is kind of a major deal and I know Groove on android is one of the few apps that is significantly worse.
Most (all?) standard Android music apps allow you to connect to Cloud or even NAS storage. You don't need Groove for it to work. So you have no issues streaming music. If the standard music app didn't you can easily download one that does.
-I'm a productivity guy and I'm all in on MS services. I have three Office 365 accounts (personal, office and college) and not being able to manage my e-mail, calendar and using office apps is totally a deal breaker, bc I usually complement powerpoints or edit spreadsheets on the go on my W10M
I have Office 365. I have Outlook (has calendar), Word, Excel and Powerpoint on my tablet and phone. Is there something I'm missing here?
-I'm in love with Cortana. I like the fact she has personality, unlike Google Now. I also like how she truly learns from me, such has understanding when and where I work, the kind of news I like to read and most of all location based reminders, which are amazing for me since I have irregular schedueles and a really crappy memory
Can't say much here. They were bringing Cortana to Android but that seems to have stalled. You're right that Google Now isn't 100% the same but it does have some good features as well. I personally don't care about the personality aspect myself.
I know that sounds like settling, but the app gap really isn't major for me. Instagram and Twitter were just about the only two daily apps that I wanted updated. Well, that and WhatsApp and Messenger, but I've all but replaced them with Skype+Messaging (since most of the people I talk to mostly are on W10 too). I ditched all news apps for the amazing RSS Reader NewsFlow, so I don't miss news reading apps either. That kinda sums up my use of an smartphone: News Reading, Listening to music, exchanging message and being productive (Wunderlist+Outlook+Slack = <3).
It's only 'settling' if you don't get what you want out of something. You seem happy enough so there's no issues.
That said, what do you see in W10M that you haven't found on android? Do you think I can get all of those things done in android?