I shopped in that area back when I was looking for a house. Ultimately, I bought in the Castle neighborhood, just a walk across the pedestrian bridge of Park De La Cruz, because the prices there were even more affordable, but of course the neighborhood is nice. Park De La Cruz and the Cherokee Point neighborhood are where I walk my dog, so the contrast between Castle and Cherokee Point is obvious to me.
In Cherokee, the majority of the people keep up the front of their houses and yards. Lawns are mowed, houses are well painted and maintained and fences are mended. I notice this because in Castle very few houses have well kept yards and houses. This is probably because you have more homeowners and fewer landlords in Cherokee. Todd Gloria used to live in that neighborhood before it got redistricted out of District 3. The owner of Marie’s Cafe in North Park also lives in that neighborhood.
Of course, Wightman St. is more disheveled because it’s zoned higher, as is anything north of University (Teralta), but for the most part houses south of Wightman are just as nice as houses in North Park in the university/805/thorn/north park way quadrant. Definitely better than houses north of University in North Park because there are not as many gigantic apartment buildings.
If you are set on getting a starter home instead of a condo, Cherokee Point is a good choice. Be prepared to have heavy competition though because it is a small neighborhood with lower prices. Back in 2009 it was almost impossible to beat the multitude of all-cash offers that were coming in for that neighborhood, I imagine it’s only worse now.
Also, FYI, that YMCA will be relocating to El Cajon Blvd (where Pearson Ford used to be) within the next couple of years. Todd Gloria said they already have several potential tenants lined up, but I’m not sure what they’ll be.