Besides using Google earth satellite, here is my favorite map of hotels.
http://anaheim-attractions.10-best.info/disney_map.pdf
If you stay at a
Disneyland resort hotel you have 3 options
1. Grand Californian (Most Expensive)
2. Disneyland Hotel
3. Paradise Pier
There is a monorail that can take you around the resort & park from those hotels. Those hotels will probably have a room big enough to hold 50 people. If you are looking for more budget friendly accomodations, then look at that map link above.
The best places are on Harbor BLVD between the Howard Johnson and the Ramada Main Gate. I have stayed at the Howard Johnson (A personal Disboard favorite), the Carousel, & The Tropicana. All those hotels (And several are motels which may not have a room for 50 people) are walking distance from the main entrance and no shuttle is required to get you to the parks. The Ramada may have a meeting room though cause I know Ramada's near my home have them. I would definitely call them. Hopefully other Disboards have answers regarding meeting room hotels. But if you stayed in an off site hotel that is not along the strip on Harbor Blvd, then look into ART Transportation. Its the Anaheim Resort Transit which has shuttle busses that go from Disneyland to the bus stop closest to your hotel. The buses run every 15-20 minutes. The bus loop is just outside Disneyland main gate which is very convenient. I believe ART is $3.00 per adult per day for unlimited use.
As for crowds, I go every late year during late may/early June, or the first 2 weeks of June before the kidlets get out for school, and the crowds are not bad at all. Its very manageable. HOWEVER!!!!! From what I understand, this year you have 2 new rides opening on June 3rd. The Little Mermaid, and Star Tours (If I have the Star Tours date wrong someone please correct me). These have been very highly anticipated for a long time, and will bring in some hefty crowds, so be prepared.
Weather: WONDERFUL! Shorts, Tshirts weather, and if your on a wet ride, you dry in under 15 minutes. Bring sun block, as well as a light jacket for the evening or first thing in the morning, but at times we didnt even need it.
Any other advice: Coming from WDW, your going to be shocked at the size of Disneyland. It's going to be tiny in comparison, as everything is within walking distance, and the 2 parks face each other, being like 200 feet away from each other. Downtown Disney is also attached to the opposite end Disneyland Esplanade in between both parks. Just remember its just as magical, its the original park that started it all, and has rides and shows that WDW doesnt have. ENJOY!
