One thing about the really expensive house nearby is that they found ways to actually use the land…maybe it wasn’t as steep a slope. But I suppose whoever buys the flip house could spend the additional $$ to do that themselves. (Probably less elaborate!) In which case I would figure that the interior finish of the house would have to be sufficiently sophisticated/high quality to attract that kind of buyer.
I gather you can’t put a dumpster at the top of the driveway?
In my neck of the woods home buyers will not look favorably on decks built without permits! I suspect CA buyers are pretty similar when it comes to decks. It is a (small) safety assurance, as cb said.
It’s hard to get an idea of the steepness of the hill from the satellite photos, but here’s a streetview shot from the apartment (condo?) complex below up to the $3 mansion:
I think that establishing a couple of terraces would be the only way.
If the coastal commission is involved, it might be a challenge to do terracing. And, it is expensive.
^ Several houses along that row have extensive landscaping and terracing. So there must be some way to get it done.
I’d think that permitting would need to be done for the deck because of earthquake requirements, and will help with selling the house.
When we had our roof done, they replaced some plywood sheeting, but no permits were required.
Roofing - our plywood underlayment is in good condition. No permit is required to tear off the FOUR layers of shingles on the roof, and put on new asphalt shingles. It might ‘technically’ require a permit if we decide we need to change out the flashing around the sides of the house, but we won’t really know that until we get everything off roof and can see the condition underneath.
Normally, a homeowner hires a roofing company and they are the ones who will or will not pull a permit. My roofing guy is the foreman for a large roofing company and he does my roofing for me on his days off - weekends. I know for a fact that they will not pull a permit for a new roof that is just new shingle layment.
The slope of our lot is very similar to the great street view from below that notrichenough posted. Good detective work finding a good photo of what we are dealing with.
I was able to confirm on Thursday with the City that the property is not located in Coastal Commission zone (monitored by the State Coastal Commission) OR in the City of San Diego Coastal Zone which is designated by the City Planning Department. For this reason there is hope that I might be able to convert the garage under the house into living space. She said that if I can bring in a copy of the original building plans from 1950 from the County Assessor’s Office and then get the 1970 plans, it will show that the original house was built and zoned for 1 car garage. The 2 car garage was an addition to the house and it is not required to retain those parking spaces.
In addition, since I am not governed by the Coastal Commission I can do simple terracing of back slope without a permit or Planning approval. We can do 3ft retaining walls without permits or review. I am planning to do two sets of 3ft retaining walls to level out a bit of the slope at the top. It’s really for psychological reasons… provide a little flat buffer that can be used for gardening if someone wants. And, it will provide a little walking space outside the downstairs area if we are able to convert it.
Have you figured out how you will get the dumpster in yet?
Also, I’m intrigued by the four layers of shingles situation. Here in the east, we never layer shingles. I wonder if it’s a practice related to the weather.
PROGRESS UPDATE:
I had to loan out my lead carpenter yesterday to the young family that is trying to finish their remodel while living in the house. This is the daughter of my retired contractor friend. She called and begged if he could come finish installing her bathroom cabinets and faucets. I said “Well, it’s probably a little more important for your family to be able to use the bathrooms than me tearing out some walls”
So, had a couple of guys doing dump runs to clear the mold plaster mess out of the garage and another guy who is quickly putting drywall up over our new headers and post and filling in all the holes in wall created by Electrician who rewired the original portion of the house.
My agent came over yesterday morning and we went through a lot of design decisions. I’m ready to move on the kitchen design. She agreed with my decision to do the kitchen in a ‘sleek contemporary’ style. Long discussion on whether buyers are OK with an IKEA kitchen. She has never encountered buyers that would not purchase a house just because it had IKEA kitchen cabinets - the quality of the IKEA cabinets is much improved now. The reason I am going to install IKEA kitchen cabinets is not because they are less expensive (sometimes they are not less expensive than what I can get with discounts) but because of the style. When I was doing the remodel at the Del Mar townhome for the single mother, she wanted that ‘flush sleek’ design for her kitchen. We searched several places in San Diego and it was very clear that IKEA was the only one that had that design at a somewhat reasonable price. Most other sleek design cabinetry was custom made or very low quality.
So, I’m very excited to do my kitchen design this weekend. I will share some of the decisions I’m making as we go along.
Ooooo, kitchen design. My favorite part of renovating a house!! Can’t wait, cb!
The four layers of shingles (I cannot confirm that… my roofing guy claims there are four layers) happen over time from unscrupulous roofing companies. In order to provide a low bid to a homeowner, they just keep throwing layers on the old stuff. It costs a lot to tear off old roofs and get a dumpster, etc. My concern is that four layers of roofing is very heavy and it starts to compromise the weight on the trusses and other parts of the structure.
We are going to need a dumpster in order to trash off all the layers of shingles.
My roofing guy is going to call the dumpster company they use. It will be delivered on Friday afternoon and be picked up first thing on Monday. There is room for the dumpster on the street, but technically it is supposed to be 10’ away from each driveway. Don’t ask me why… I’m pretty sure that if I get a dumpster placed in front of my driveway that it should be OK since I am the homeowner. No room to put it in the small driveway leading to 1 car garage and absolutely no way to get a huge heavy dumpster with wheels blocked safely on the steep driveway.
So, the dumpster will be blocking my one car driveway for the weekend and mysteriously disappear by Monday morning.
KITCHEN DESIGN
Here is the ‘style’ that I am going to be aiming for. This type of style goes well with the style of the house after I change out the garage door in front and change up the curb appeal a bit. I’m going to try to mix up the cabinet colors, hopefully in a tasteful way 
http://www.houzz.com/photos/3498689/Fait-Avenue-contemporary-kitchen-baltimore
http://www.houzz.com/photos/237194/Lauder-contemporary-kitchen-toronto
http://www.houzz.com/photos/271729/Kitchen
http://www.houzz.com/photos/799072/Elegant-White-IKEA-Kitchen-modern-kitchen-toronto
http://www.houzz.com/photos/2076037/East-23rd-Street-contemporary-kitchen-new-york
http://www.houzz.com/photos/454917/LG-House-Kitchen-contemporary-kitchen-edmonton
Kitchen Decisions:
I hope that you can visualize this from the photos…
Back wall against garage - there is 10ft available between the garage door and wall
Counter depth refrigerator at left
24" set of drawers and 24" upper cabinet (for glassware)
36" gas cooktop with deep drawers underneath for pots and pans
24" set of drawers to right with 24" upper cabinet for plates
Side wall on west - there is only 4’ available here to allow for comfortable walkway to garage
Ceiling height cabinetry with 30" convection microwave and oven combo in wall
18" tall pull out pantry
Island that will be installed pushed out into current living area
30" sink (cannot get any larger sink into the space)
Dishwasher
Trash pull out with drawer at top for silverware
I realize that there is just not a lot of counterspace in this kitchen, but I’m hoping that the island will give the illusion of a lot of counterspace. It will be extended 12" out at counter height for stools and eating on living room side.
We are leaving the wall of custom built cabinets and shelves across the dining area which will provide a lot of storage. Hopefully that can be used as food storage/pantry. There is just not enough room in the kitchen to do anything more
I like the East 23rd St look the best. It is probably just me, but I can’t stand those base cabinets with the wood grain going sideways. They just look like ultra-cheap veneer to me.
I think the handle style makes a big difference in this look between a quality look and cheesy-looking.
It does give you the opportunity to do something interesting with the hood. 
what will the dimensions of the island be?
In order to open up the views in this house, I wanted to move the main post (see photos) as far to the left as possible - viewing from the front door. Viewing from the living room back to the kitchen - the post was moved as far to the right as possible with structural considerations. The post itself had to be pretty wide because we wanted to make sure that we have at least 4" of each header (there is one to the left and one to the right) resting and strapped to the post. So the post is a very beefy 4" x 8". The cabinetry will butt up against the post with no drywall and will be drywalled above the countertop only and the sides facing out. I have to create false bump outs on the post above the countertop because I want to get one outlet and one landline telephone connection in post above countertop.
Because of the position of the post, it has to be positioned to the right of the island (looking out from kitchen to living area). I insisted on 36" walking room to the left of the island. This leaves us only 72" wide island to accommodate a 24" dishwasher, 30" sink and 18" trash pull out.
The configuration will be… from left to right looking out from kitchen to living area
Dishwasher
Sink
Trash pull out with a silverware drawer on top
This allows for silverware to be put away to the right of the sink above trash pull out, glassware to be put away to upper left of stove and plates in the upper cabinet to right of stove. Pots and pans will be under the large 36" cooktop
So we have one vote for the plain white glossy cabinetry. For some reason I kind of like the wood grain sideways look, but I can see your point about it looking fake and kind of formica’y
I would love to have some fun installing color cabinets but I know that it would turn off a percentage of the buyers, especially older clientele. If this was a downtown condo catering to urban hip younger crowd, color cabinetry would be the correct design choice.
The cabinetry installed in the Del Mar Townhome remodel were a lovely ‘creamy’ color instead of plain white. There is also a grey glossy cabinet color choice.