La Cumbre Plaza is right between Hope Ranch and where I grew up (other side of State). When I was a kid, Five Points (the other side of La Cumbre) was the prototypical atomic era strip mall, anchored by a Thrifty's with a lunch counter, where the ice cream was $.05 per scoop. It got it's upgrade to Moorish when I was in junior high school.
Until Paseo Nuevo opened in 1991, La Cumbre Plaza was the place to shop in Santa Barbara. My mom bought "Toughskins" for me at the Sears, my dad bought tools at Sears, a treat was going to Kayser's for a Kayser's Krush (that will take you back, CM). I did all the youth programs at the YMCA next door (swim lessons, YBA, Youth and Government) - my mom would give me a two dollars and I would walk to the Y, and on the way back I would stop at Char West and get a taco and a 7-up slush. Many high school friends worked at the mall (I did two summer tours there myself). La Sumida was the nursery across the street where my parents bought all the plants for the yard (on an aside - Pat Sumida's family was interred during WWII, had all their land taken away, and had to work to buy it all back after the war - Sumida is now one of the largest individual land owners in Santa Barbara - good things happen to good people in the end). Christmas season was 70 degree days, and the sound of the Carillon at Robinson's playing Christmas carols on the hour.
When the mall originally opened, Robinson's (a So. Cal. department store that was eventually bought by Macy's - the Macy's at Fashion Island was a Robinson's originally) and Sears were the anchors. This was when Sears was "the" American retailer (if you grew up in the seventies or earlier, you remember the "big book" at Christmas). There were a few other chains in the mall, but most of the stores were local. During the eighties, more chains pushed into the mall (Pottery Barn; Gap; Banana Republic - during their early Indiana Jones, surplus, jungle themed retail days; Eddie Bauer; some lame outfit called AKA Joe; Red Robin, etc.). Most of the locally owned business' could not compete, and left as the economy soured in the late eighties and early nineties. The opening of Paseo Nuevo downtown with it's Nordstrom's (oh the excitement - a true high end department store - my mom was a twitter! And they bussed in patrons from Bakersfield!) put a serious hurt on La Cumbre Plaza - until then, there was not any major shopping downtown to compete with La Cumbre Plaza. The major chains tried having two locations, but there was not enough traffic to justify it for most of them. The mall has tried to remake its self as upscale for about 15 years now, and in the process has bastardized the look of the mall. If you go to the north end parking lot, you can see the original design elements at the Macy's - a clean, somewhat modern take on Mission influences (you can see the same look at Fashion Island from the south parking lot looking at the Macy's). They have added all sorts of architectural elements that do not fit the scale, or other features. They are so out of place that when I see them, I envision workers using a hot glue gun to paste them on - like they are some type of Hollywood foam.
I think that Sear's owns it's location, which probably explains why it is still there. I also understand that certain departments still do good business for them.
The entrance you talk about (off the north bound 101) isn't original. The original entrance was from State St. over a planned bridge towards Robinson's (I do not believe the bridge was ever built - but the entrance is at that location). In fact, there was no through road on the east side of the mall - I had never thought about how that looked to a first time visitor until you mentioned it - I guess that is something for the planners to consider.
A note on Paseo Nuevo - it was built in a part of town that was in pretty bad shape - in fact, when I was in high school, it was the "dangerous" part of town after dark. Bars such as the Off Ice (now O'Malleys) were notorious for their hard core clientele (back then UCSB students stayed in IV to party - that is a topic for another post: "UCSB glory days during the late eighties and early nineties

"). The area had been in decline for some time, with Ott's hardware store finding tough times. Ironically, the tough times began with the opening of La Cumbre Plaza and Five Points. A massive redevelopment project was undertaken in the late eighties, in conjunction with removal of stoplights on the 101 (you read that right). The mall is considered one of the greatest redevelopment projects in California history, for the economic, preservation, and aesthetic rejuvenation it brought to the area. One of the anchor tenants is a major bookstore. Another major bookstore moved in kitty korner to capitalize on the traffic (and provide a forum for Mason B. Mason

). These two placements wiped out the Earthling Bookstore, a local favorite. The new mall also put the hurt on mid State locations such as La Arcada (goodbye WA King and Andersen's), and the area next to the Arlington, as well as the afore mentioned La Cumbre Plaza. I guess the whole thing can be filed under "Best Intentions and Unintended Consequences" and "Watch Out What You Wish For".