San Diego is a great town, loved it, even opened a real estate office there in a prime spot by the Shadow Ridge Country Club area in Vista ( It was ground floor time) and another in a little one room setup in La Mesa, and lived near Bird Rock.

I did a gut rehab on the 1700 block of Wiely st ( 17th & ridge ave area )The three story row cost was $ 180,000I’m not sure what you can do with $75kBe careful!!!  

http://www.zillow.com/homedetails/422-Timberline-Ridge-Ct-Winston-Salem-NC-27106/60299709_zpid/How would you go about deciding which way to go?

I wouldn't be that concerned about it myself, if you are, get an engineer out there, make sure they don't give you a load of stuff and tell you the house will fall down.....I'd be concerned about the soil being unstable, might look around at other houses in the area, as you can, and look for settlement.....which may be seen in the ridge of any roof BTW.

hey Mike I live in wheat Ridge Colorado just west of Denver.  

How many ridges, hips, and valleys are there?

Newer homes generally escape with repairs, primarily to ridges and valleys, which are the most easily damaged. 

If you do not get the moisture out, the cupping will get worse ... you will also get mould growth under the floor.If this is a rental, and you can get the floor to lay down enough people are not catching feet on ridges, I wouldn't change it until the current tenant leaves.  

My realtor is pitching a development there pre-contruction called Maple Ridge.

. $400 Install gutter down spout $75 clean gutters $120 Insulate basement ceiling $30/hr labor rate ***plus matieral*** Seal all gaps on furnace ventiliation ducts $100 Installation of continious ridge venting. $1200 remove 1st floor bathroom ceiling inspect for mold and water damage, install new sheetrock, finish, and paint $650 Additional cost based on extent of plumbing repairs needed. at labor rate of $35 per hour Install 2 glass shower doors 1st and 2nd floor bathroom showers, $140 plus cost ****$150-200 per shower door**** replace broken/missing glass in attic window $60 replace broken glass in basement window $40 Replace front porch ceiling $600 Install drain pan and waste line from 2nd floor hot water heater $160 extend sewer ventiliatin line thru roof. $300 correct 1st floor shower water lines by reversing the cold and hot water. $150 Run electric for condensation pipe in basement $120 Run drain line from condendation pump into waste water drain, $70 Replace all attic duct with flexible insulated duct. $6 per linear foot Mortar interior section of chimney inside of attic $400 Mortar exterior section of chimney $600 secure all loose electrical wiring in basement $85 Tearoff and replace south side of main roof, $4400 Additional cost may apply if board replacement is needed due to rotting or broken boards.No quote on the foundation yet.