Oregon has some good opportunities, but it's not a great place for a new hunter. Especially living near Portland. Success rates are low for most general hunts, the controlled hunts are confusing for a beginner and in the process of changing, land ownership and access on private timber is complicated, and if he's trying to stay within an hour or two of Portland... well, so are a half million other people. Give or take.
Have him look up ODFW harvest stats for the general seasons to get an idea what he's in for. They're hard to read, but most units for general deer will be single digit to low teens for a success rate. It's tough hunting, but obviously not impossible. So take that for what it's worth.
https://myodfw.com/articles/big-game-hunting-harvest-statistics
Hunter education isn't legally required for adults in OR, but he should do it anyway. Take an online/at-home version that involves a single in-person field day. Start here to find a class.
https://myodfw.com/articles/hunter-education-course-or-field-day-registration
ODFW also occasionally offers workshops for new hunters, look into this (they've even held semi-guided pheasant/waterfowl hunts for newbies in the past, not sure if they still do)
https://www.dfw.state.or.us/education/
Does he have any friends/relatives with land in the area? If so, this will really change things. I wouldn't recommend a brand-new hunter start knocking on stranger's doors asking about hunt permission, but if there's already a place with a good relationship they might be open to it. If this is the case, he should look into the new general antlerless elk tags, landowner permits (LOP) if they have enough acreage, or just using a general tag on their land. If he can access farmland near, say, North Plains, he's got a good shot at taking a cow elk - but he better have significant backup and a very understanding landowner. If he doesn't have private land access with an understanding landowner, and some support to deal with the animal, do not buy this tag.
If he has farm access elsewhere in the Willamette Valley, he might apply for the 615 tag (either-sex deer). Make sure the land is actually in the Willamette Unit though, and if he doesn't already have this kind of access... seriously, don't apply for the tag.
Otherwise, pick an area in eastern Oregon he knows from other outdoor activities and apply for a mule deer rifle hunt there. It'll be in the beginning of October, some aren't too bad to draw. Mule deer populations have been on the decline but he could still have a good hunt with a modest success rate.
If he wants to stay closer to home, look into the western general rifle deer season. It's a long season (by western standards), covering most of October, for a buck deer anywhere west of the Cascades. All he needs are boots and a rifle. He'll need to understand land ownership and access, as much of the land is privately owned industrial timber. This is a good place to start.
http://www.eregulations.com/oregon/big-game-hunting/cooperative-travel-management-areas/
Lastly, I just noticed you mentioned he wants to "try" hunting. If that's the case, he's probably better off going on a pheasant hunt somewhere (state wildlife area, like Sauvie or EE Wilson, or private reserve), or visiting you in a place where you can essentially "guide" him. Oregon can be tough hunting in all respects, and he'll need to be pretty motivated to get past all the hurdles.
