We’re headed to SoCal in October to use up some timeshare points in Carlsbad. We’re close enough to DL that my DD12 and I want to check it out. Due to a scheduling quirk we can either spend Fri & Sat night in Anaheim for 2 days at the park or drive up from Carlsbad mid-week for a 1-day (no night) quick peek. Crowd calendar is showing 8 for the weekend, 2 midweek. If maxpass isn’t a thing come this fall, does the crowd difference nullify having that second day? We were just at WDW so our focus will be on things that are different at DL.
Obviously this is all contingent on CA’s visitor rules come the fall…
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Personally I would go for two days, assuming it is basically two full days. On the one hand, lower crowds and shorter waits will make it a much more pleasant experience.
On the other hand, there is never a guarantee that crowds will be low, even if it’s perfectly logical to expect low crowds (non-holiday weekday in October). Also, park hours are usually shorter on low crowd days. So there just isn’t enough time in one (short) day to do everything you will want to do in DL and DCA, even with low waits.
That said, if you were a DL veteran and knew exactly what you wanted to do, I might go the other way.
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I haven’t been to DL since 1980 so the “veteran” label doesn’t apply 
Thoughts about onsite vs off? It doesn’t seem like the astronomical prices for Grand Californian hotel are balanced by many timesaving perks. The whole open for reservations thing later this week is what jumped started the planning on this.
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Glad to know it’s not a crazy idea! I can see pros/cons of each option, it might come down to whether it’s the larger (slower) group or just my DD and I. Not sure I’ve got the energy for an all nighter any more 
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The Grand Californian is a beautiful hotel and the staff are amazing! I have been blessed to stay there 4x and twice were in the DVC Villas. Disneyland Hotel is also beautiful ( I just love those light up firework headboards! ) and honestly my favorite onsite. Although I have yet to stay at PP hotel I can say I do want to stay there once! Their breakfast buffet is amazing!! These places are crazy high in price and I can have 7 trips offsite compared to 1 onesite. I have been treated good at all the hotels along Harbor Blvd. I would say my favorite would be Park Vue Inn, Desert Inn, Tropicana Inn or Grand Legacy. Desert Inn will be lowest in cost and Park Vue probably the highest but it is also the closest to the crosswalk that leads to the entrance.
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The Anaheim Hotel and the Fairfield are also favorites of other liners but I haven’t stayed at either. Not sure if they are doing the free breakfasts but I know Grand Legacy wasn’t two weeks ago and Desert Inn hasn’t opened yet. Totally not a crazy idea and you will start getting the energy once the planning begins! 
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If you are on a budget, absolutely stay offsite at a Harbor Blvd Hotel. Fairfield Inn, Courtyard, Howard Johnson, and many more are all good values for what you get and as close to the park entrance as DLH or PPH.
If you want the premium experience, on-site is the way to go. My favorite is GCH due to proximity - you literally can’t get any closer to a Disney park. But Disneyland Hotel is wonderful too. I haven’t stayed at Paradise Pier because it’s too expensive compared to the Harbor Blvd hotels and not any closer.
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I forgot about the entrance into DCA!! That has saved me a few times getting into park and by passing DTD!
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Traffic into Anaheim from Carlsbad is an issue as well. My parents had a timeshare down there in Carlsbad. Gorgeous property/town. Bit of a hike to get to Anaheim. Way more so with traffic each way. Growing up down there, my advice is go for the two days instead of tiring yourself out getting there and back.
Grand Californian is my all time favorite of the resorts down there at DLR both for ambiance and ease of use. That separate entrance to DCA is everything. That being said, I also know what they charge for those nights in October and man, that’s rough. There are several options for all budgets within walking distance off of both Harbor or Katella. Harbor is closer walk, Katella might have nicer places to stay and an Uber or cab can get you there if it’s too far to walk.
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Also, for those wondering, UBER drop-off is on Harbor, just South of the pedestrian entrance to the parks. I’m not sure if there’s a separate one closer to DLH for DTD.
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There is an Uber drop off near DTD. If you head out of DTD towards the parking structures, it’s to the left. I prefer this drop off. It feels closer to me than the one on Harbor.
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