I'm looking at purchasing a DSLR - I mostly use my iphone currently and I have a point and shoot but I'm not crazy about the results I've gotten from it so i rarely use it.
iphone - Pros: I always have it with me, I never use the flash and the photos are easy to put on social media and look good on a screen. Cons: Horrible print quality, I never seem to back it up to my laptop and my iphoto is now horribly unorganized
Point and Shoot: Pros - small, easy to charge, takes good photos in natural light w/o flash, Cons - I can't seem to capture the images I want, either a sec too late or too early, clunky and slow in that i cant take photos in rapid succession (not burst), Pain in the ass to upload to social media/share with others, but it forced me to keep my laptop's iphoto organized and my photos backed up.
Also my laptop is aging (2009) and I rarely use it at home. I mostly use my desktop at work and don't find much time to be on the computer in the evenings.
I'm not a photography novice, I've taken quite a few photography courses over the years however most of them were with manual SLR and film. but I understand the basics of camera function (iso, shutter speed, aperture, etc)
i'm looking at the Canon Rebel T5 or the the Nikon D3300 both are in roughly the same price range
I'm leaning toward the Nikon because of high megapixels and built it wifi.