Ok so here is the my quandary, I am planning on going north towards Alaska (driving through Canada during the month of May/June) as my annual road trip.
I want to buy either an old 1990’s Jeep wrangler or a 1990’s Subaru forester for the trek. I’ve heard finding parts to the Jeep is a dime a dozen, but the Subaru would be less likely to break down. Yesterday I listened to an old Car-talk episode talking bout how awesome and fun a jeep is and now I think I may have caught the Jeep bug, because I now desperately want one 
The question is more reliable as an old timer to go with, I can find both at relatively the same price 1,000-1,500$
I am planning on taking my pup with me and a few supplies for the car ride.
any insight would be most most appreciated
If you are staying on the road take the Subaru, heck take anything! If you are going off road take the jeep.
Why restrict the choices to these two vehicles? A Ford Ranger with a 4 cylinder and manual transmission is more idiot proof, more easily repaired and parts are more readily available than the Sube and Wrangler. A winch and individual control of the parking brakes will get you through any reasonable difficulty as well as 4x4 without all the added potential break downs.
I felt like the awd and the 4wd features where important when going up to a place like Alaska especially if alone
The reason I chose those two (models I should say) is because I can potentially sleep in both of them the cab size into consideration 
the ford ranger is a good idea, if it was not for the two seat set up
Anything that old is likely to have problems. I’ve never been too impressed by the reliability of Subaru vehicles, though old Jeeps aren’t the soul of reliability either. One thing for sure though is that if the Jeep breaks, it’s much more likely that you’ll be able to get it fixed almost anywhere, and cheaper than the Subaru.
I think you’d be better off with a Grand Cherokee than a Wrangler if you’re going to get a Jeep. Wranglers are really unpleasant on long highway trips. They ride like crap, handle not so good, are drafty and noisy. It’ll be hard enough to get any car to be comfy and warm with Canadian/Alaskan winters—the soft top Wrangler will be really unpleasant.
I’d also prepare for the trip: Keep blankets, snacks, water, and anything else that you think would be handy in the event that somehow you get stranded and can’t get help for 12 hours or more.
Both of those vehicles are popular here in Alaska. If you are coming up in May you really don’t need AWD. The roads are clear of any snow that time of year. If you are planning on doing some off road driving then the Jeep is better due to the higher clearences it has. I have owned Subarus for a lot of years but I don’t do off road trips with them though some folks do like to.