Theoretically, if you could position yourself at the event horizon where time slows down in relation to a black hole, and then somehow managed to escape it’s pull after say a year and travel back to earth, how far into the future would you be, and in theory would this even work?
Also
If you could do the same thing and transmit an image back to earth, would we be able to effectively “look” into the future even though time has not slowed for us?
Hovering near the event horizon of a black hole would cause time to pass more slowly for you than for a distant observer. How much time would elapse on Earth while you performed such a maneuver would depend on how close you get to the horizon. Theoretically there is no upper limit.
However, this scheme cannot be used to provide images of the future.
Because whenever you go then you are. 
What if you sent a probe down to the event horizon designed to look out at the universe and it was sending results through a cable tethered to a data collection point much further out? Could that be used to gather information about the future or would the progress of the data up the tether be limited?
The signals sent back via the tether are subject to the same time dilation as the probe, so you would get the image of your future at the earliest when that future has already arrived.