I was wondering if anyone has advice about taking the train from California to Indy. Can I expect delays and stops along the way. I was hopeing my friend will be with me to board game on the way but that is up in the air as of now, so does anyone have any traval tips.

I'd looked at doing Amtrak for awhile and gave up on it for several reasons.

First, it's pricey.  Train travel is surpisingly expensive in the US.

Second, it's time-consuming.  If you're okay with slow travel (I am, but three days on a train can be quite a lot) that's not necessarily a bad thing but keep that in mind when making reservations.  If you go with the coach seats that's basically two or three days sitting in close proximity with 83 other people, and no shower access for most of it (not joking here).  If you get a roomette or above you get privacy, access to a shower, and meals are included but your price will literally triple.

Third, there are no direct trains so you're due for at least one transfer to Indy, most likely from Chicago.  The cheapest options put you on a bus, though there are a few trains from westbound that go into Indy (I was looking from the east coast and everything put me on a bus).

Fourth, train travel can be taxing on some people.  Our last train trip was from DC to the Grand Canyon, and the first day on the east coast all the trees flying by made my GF quite motion sick, though this disappated once we hit the open plains of the mid and southwest.  Sleeping onboard a train can be disruptive, not just due to the movement (I actually find it soothing) or the sound of the rails (same) but because the train is legally required to blast its horn at every roadway intersection (I'm a heavy sleeper but she keyp waking up).

That said, here are the upsides:

First, when you get off the train you're in the middle of the city.  There's no airport transfer to deal with, you're just there.

Second, trains have almost no luggage restrictions, unlike airlines, so packing costumes or taking home lots of purchases becomes a lot more manageable.

Third, train travel is very relaxed (see point about time consuming).  If you like leisurely travel, it's a great way to take some time to relax and watch the world go by.  Catch up on your reading, listen to podcasts while watching the scenery fly by, or bring some games with and set something up in the observation car (or your roomette if you have one).

I like train travel but ultimately passed on using the train to get to Gen Con.  It's too pricey and inconvenient to me to be worthwhile; I'd rather pack a few friends in the car, split costs, and make a road trip out of it.  That said, if you have the time and money, make a vacation of it.  Go with a roomette and make a trip of it.  The roomette gives you privacy and includes your meals, as well as juice, coffee, tea, and the like (we brought a flask as well).

I thought about taking the train from NY, but it was an overnight trip from NY to Chicago, then wait all day in Chicago and take a PM train from Chicago to Indy. Same for the return trip. This would have added 2 exta travel days. It would be nice, but as stated above we can get 8 people in a van and make the drive in 12 hours, and split the cost.

I've looked at the train into Indy. What's stopped me, honestly, is only the exact arrival and departure times. IIRC, I'd get into town very very late Wed, and have to leave before dawn or so on Monday. Now, I do the Wed-Mon thing, but I like getting there early Wed and staying past breakfast Sunday--it's my only time of the year to be able to hang out with certain friends.

Otherwise, it's actually really good timing for GC, that Indy-Cali Amtrack train.

I've looked into it myself and wanted to do it for ease of transportation (not having to deal with Indy parking). Not much the time involved but the costs were not worth it. I can kinda see if it was just myself but anybody that can/does travel with friends/significant other almost always more economical to drive in. 

Much as i loathe being the designated driver year after year the money saved by splitting the cost with even one other person makes the effort worthwhile. 

Do the math and see if the value gained (be in relaxation, not having to deal with car, etc) is worth the extra expense/planning.

How insensitive. :)

We took the train to Gen Con one year from Chicago, and it was a great experience. There were several people on board who had been taking it all the way from Seattle and we had a great time meeting up with them and playing board games for our entire trip. We haven't been to Gen Con in a couple years now, but the next time we go I will probably consider the train again just because it was so nice not to have to drive and to enjoy hanging out along the way. Really, it all depends on your endurance with regard to being cooped up on board for multiple days. If you're someone who already loves train travel, you'll be fine. Also, there are always people to play board games with on trains. Always. I've taken plenty of solo trips and I have yet to take a trip where someone hasn't been happy to play at least zombie dice with me.

That said, my one word of warning: the Indianapolis train station is awful. When we were there it was disgusting, there was very little in the way of vending machines (and what they did have barely worked,) there was this obnoxious loud humming noise the whole time... and we had to wait several hours to board because we hadn't booked our hotel for the last night. So, you know, if you're going to take the train do yourself a favor and either book an extra night in your hotel if you have the 5 am train out OR lug your suitcase(s) down to Steak N Shake or some other 24 hour joint to pass some of the time, because you'll want to spend as little time at the train station as possible. 

Interestingly enough, if you book trains through Amtrak around Gen Con, they offer downtown hotel rooms.  They're at very high rates ($500+ per night) but you can get them with your train ticket.