Noobies VÜ

Once again I take up my hammer to try and make some improvements to my house. This one is gonna take a little time though, couple weekends worth.
My house is an odd house dear readers, it's kind of a stupid house, it's also unique and I do like it, but damn, every time I try to improve it I run into the idiocy of the former owners.
It gets wretched hot upstairs and I have a real difficult time dealing with it. It's one of those things that I find myself surprised that the people who lived here previously tolerated it. 
I was dubious that there was any insulation on the rear wall and the outside sheathing is looking really bad so I decided to put up some vinyl siding. After an annoying experience with an asshat for customer service at Lowe's (apparently I shouldn't shop for things on Sundays- duh.) I wound up at Home Depot and I found some really inexpensive siding.
Just a little aside, Lowe's has a ton of siding on their website, but they tell you there are 4 profiles and 12 colors, I challenge someone to locate them. Home Depot on the other hand doesn't have anything on their site except for fixture mounts. WTF? This was the reason for my trip to Lowe's but look out! Lowe's doesn't carry siding in their stores, you have to special order (just don't try to look for samples on a Sunday). But Home Depot actually carries siding.
Back to the siding I found at HD. They had a single box of 4.5" double lap for $46! They only carry 5" double lap now I guess. I can also tell you a single box will help no one. Except me! I only have to cover the upper bit above the back roof and it's 32' x 32" and this is more than enough for that. Just FYI, a box of siding is normally $158.
Here's the tragic back of my house, don't judge me I have a budget. lol