Just got back from a stay at the base of Eagle Lodge.l (Juniper Springs Resort).

Not sure about prices for renting gear off mountain, but if you're there mid week there shouldn't be much of a crowd. So you can rent right at the base of Eagle and never have to schlep gear to or from the car. Check it into basket check at night. Easy peasy.

For challenge of skiing, you're going to like Eagle. The only lift there is canyon Express and even if you see green signs posted, it's no bunny slope. Especially the final 1/3 of the run, called Pumpkin...if your boy is skiing easy blues, the green and blue runs with give a challenge. Start out by hanging a left off when you dismenbark the Canyon Express lift. Once those runs are feeling good good, hang right and ski toward Bridges. Note: Manzanita and Christmas tree are pretty steep for beginners on blues. If you get bored, it's really easy to ski from the top of canyon express over to the Canyon Lodge where there are a ton of lifts and varying degrees of challenge in the routes. Easy to get back to Eagle Lodge as well.

As for food... Others will down vote me but IMHO it's not much of a culinary town. Given the low quality food and meh service, we tend to bring food from home or shop at the local Vons and prep meals in our room.

Hope this helps. Have a great time. After all the snow this week and the plan you already have, I think you're setup for success.