I have a NEx-5 which I have had for a year now.
First to get out of Auto mode you should take a look at this book - Understanding Exposure by Bryan Peterson -
http://www.amazon.co.uk/Understandi...9390/ref=sr_1_1?ie=UTF8&qid=1328777822&sr=8-1
Also once you use the Menu system for a while it will become second nature and while it has a few annoyances once you are used to it most of the stuff is easy to get at and becomes simple to use. Shooting in iAuto will not help you learn the system menu or customise it the way that will be best for you.
It is one of the most recommended books and really will help you make the step from iAuto to A, S and Manual shooting. I found it simple to understand and yet gives you the confidence to move onwards and upwards.
I have the 16mm, 18-55mm, 18-200mm as well as 2 adapters the UWA and Fisheye both for the 16mm lens.
Now to the lenses,
The 16mm isn't the greatest lens but it's fine in the centre and adding the UWA and Fisheye(only got that today for my birthday so not used yet) gives a few options and there is plenty of room to crop off the edges if needed. Also does give you the ability to stick it on and put the camera in your coat pocket.
The 18-200mm. This is the lens I pretty much use all the time, it's big but all things considered it's not too big or heavy and is a pretty good lens, It also takes great videos of the kids etc.
The 18-55mm lens is not bad for a kit lens and is useful if you are looking for the large coat pocket set up, I have to admit I mainly use the 18-200mm.
I am after the Nex-7 if I wasn't I would be getting the new LA-EA2 adapter now that allows A mount lens and pdaf AF, sure it makes the camera bigger but you can always take it off and make it smaller if needed. I will get the LEA-02 once I have the Nex-7 but I need to spread the costs out and the Nex-7 isn't cheap.
I have thought about moving to a DSLR and looked at the D7000 and the A65/A77 but having used the Nex for a year now they just seems too heavy and bulky all the time, especially as I have 2 young kids that are normally along on my shoots.
The Nex system is let down by the Lens choice and in some ways is very frustrating however it has such a Good sensor in it I find it worth looking at the LA-EA2 adaptor as a way of adding a few more lenses I would like while continuing with the Nex system which I really like.
Shooting wise I like taking pictures of anything but as I live near Sandbanks on the coast there is a lot of sea/clouds and landscape shots as well as parks I visit with the kids etc.
One thing that is really important is regardless of the camera is that you take the shots and the more you take and the more you learn the better you will become, it is really noticable for me how over the year I have been taking pictures how much I have learnt and how things can be improved upon. Having the best setup in the world will not make you magically take great pictures.
There are lots of great camera systems out there, the Olympus M43 looks great and has some really good lenses and there are some great DSLR's to choose from and everyone has their favourites but really you need to choose what suits you and then give it a good go.
Here is my flickr link if you want to look at what I have taken with the nex Lenses etc to give you an idea what you can do, also to add in shooting in Raw format helps and learning post processing to get the most out of your shots can help (this is something I am learning bit by bit).
Sorry to waffle a bit but thought you might like some thoughts from a Nex-5 user.
www.flickr.com/photos/reemul