extend roof, increase pitch?

I have some questions regarding my wood sided house. I purchased my home 3 years ago, it is a split side house with a block and brick first floor, and a wood sided second floor. I believe my siding is called “T-111”; at least that’s what I am told. It is plywood with vertical cuts in it. My house is built into the side of a hill, so at one end of the house the peak of my roof is quite high, making paining the trim something to avoid. I had a crew install new gutters and wrapped the fascia with aluminum, and then I had them add a vinyl soffet. I have had 3 different guys come out to price staining the siding, but I am unsure how to proceed based on their recommendations. The siding itself is quite dark, but in replacing an outside light fixture I can see that it wasn’t always that way. It appears that the stain has darkened in the weathering process. One guy told me, all it needs is a good pressure washing and he can bring the old color back with a tinted stain. The next guy told me, he would need to pressure wash it and apply a colored stain, not tinted. He went on to say that the house would look like it was painted, and most of the wood grain would be covered up with color. The third guy told me that there is no way to lighten the wood, and he wants to put vinyl siding on the house. I would like to keep the wood, its different (every house in the area is vinyl) and the wood is still in excellent condition. All of the windows are flashed with copper, and there are no signs of bad wood anywhere. Anyone have any suggestions?

First off, thanks to all those in this forum who responded to my beginner questions! Your advice helped fill the very large holes in my building experti se...or the lack of. I am happy to say that I am almost finished siding my 12' x 21' shed. (odd size I know, but the interior shed is 12x16 and the extra 5 ft is an overhang that we framed up to take advantage of where the old shed sat.) Secondly, this is not a "guide" as much as an experience because there are many things that I did wrong and I hope some of the experts in this forum will be quick to point out where I went astray so other beginners who read this post will not make the same mistakes. Here we go. Difficulty - Easy once you get the hang of it. I did this primarily on my own. I have only now seen that there are little tools so one person can hang a board solo. This would have been nice but managed without one. When I was ready with a board my wife would help hold an end. (more on that later) Material - Smooth finish HardiPlank siding. It cost about .35 cents a board more for the smooth but I am glad I went with it now that it is up. Carrying boards and weight - After you pick just one of these boards up you realize that you can't carry them flat or they will break. Must be carried on edge. Some say they are heavy but I didn't really think so. Could carry 2 or three boards by myself with no issue. Nails & Fastening - I tried three different nails and ended up going with a 1 3/4 inch roofing nail. The ring shank nails seemed to bend really easily as did the 6d and 7d siding nails (I know, probably more me than the nail). Rarely bent the roofing nail. Also, definately nail to studs if at all possible. The cement fiber doesn't grab to the nail the way wood does. I went around and snapped a chalk line on the felt paper where my studs were before putting siding up. You will notice the difference between hitting the stud and not when you nail the first board. Obviously there are some points where there might be 1 or 2 nails in a board that don't have a stud to go into. For me this was usually where the board met the trim but I tried to make certain 90% of nails on a board were in studs. (I put all trim up first so I could butt the siding to it. I just thought it would look better.) I drilled pilot holes in the corners of boards before I hung them. Split the very first board I tried to hang without doing that. Don't over hammer. Just nail flush as directions recommend. Cutting - I was most worried about this. Bad dust, proper cuts, etc. Since this isn't my full time job, I didn't want to spend lots of money on blades, specialty tools, etc if I didn't have to. However, I did purchase a $30 mask with proper filters. Why spend all the money on materials, tools, etc and then cheap out on the one piece of equipment we can't replace. Our Lungs!! Get a mask, enough said. The "Hardi Blades" can be $60 or so. I used my porter/cable circ saw with a carbide blade. Cut just fine. I found a $16 dollar blade at my local hardware store that was for cement fiber and it made a big difference from the regular carbide blade. Much less dust and noise. You can score and snap with just a box cutter but is tedious. Even used my miter saw with regular carbide blade and worked just fine. I would wear ear plugs when ripping (lengthwise) the boards. This is VERY LOUD. Regular cuts arent too bad, but ripping. Wow. Also recommend cutting ourdoors as dust is crazy. Starter strips - For some reason I couldn't find any 1/4 inch lathe strips anywhere. So, I ripped a hardi board in 1 1/2" strips to use for my starter strips. (again NOISE) 1st Row - Get your first two rows correct and you are set. For my first row I drew a horizontal level line on the felt so I knew where to set my first board. 2nd Row - I cut a 2x4 to 6" (didn't have enough room to use the guages I made yet as I was too close to ground). I held the 6" block flush with the bottom of the first piece and set my end of the board on the block. My wife held the other end. Nailed in the corner, then used the block at each stud to finish off nailing the row. Checked again with 4' level (yes I am a bit of a freak.) Gauges - I made two gauges out of 2x4 studs. Cut them at 8", then cut out a 6" section. About 1/4" or so out of the narrow side. Now, I could hook the gauge under the previous row and set my board on top and have a consistent 6", level, reveal. My wife used the 2nd one to set her end of the board on. My wife helped me with many of the boards but I found a way to hang pieces solo. After I was up high enough, usually 4 ft or so, I would set my guage at one end and wedge a section of 2x4 under it. Then, I could set one end while the other was held up by the gauge and 2x4. Board Ends - I tried to leave a 1/8 gap between board and trim. I left the tiniest of gaps where the boards butted each other. I think the directions said you didn't have to leave a gap but a little one seemed like a good idea to me. Things I should have done - Paid closer attention to my Grandfather when I would help him build things as a kid. However that is where I got my, "If your gonna do it, do it right" attitude. Put a "kick board" or whatever you call it at the bottom. I had some unlevel cement issues to deal with and putting a kick board at the bottom would have made it stick out a whold lot more. Plus, I don't think it was really necessary as I am not worried about rot with the cement fiber. (no, it is not sitting in dirt anywhere or in contact with the ground) Bought a rip guide for my circ saw. Using one of those sheer tools would have been awesome for pieces that had to be cut out for windows, doors, etc. I think I should have caulked the seams as I finished a row. Didn't think of this until I started caulking the seams after I finished a side. Water shouldn't really get up there but probably would have been the thing to do. If I had a second circ saw I would have used that. I have a feeling that cement fiber dust is not good for my circ saw. I really like my saw and hope I haven't done too much long term damage. Questions I still have - How do you replace a board if one needs it sometime? It is blind nailed and trying to get the nail out is probably going to cause issues for the board above it. Any tips on cleaning my circ saw would be much appreciated. I've heard not to use an air hose. Well, I think that is about it. Hopes this helps someone here looking for info. Please post if I did something totally wrong as I don't want to screw anyone up. Cheers All!