Where/how to cut holes in beveled siding?

Hi. I am replacing this nasty rotten batten sheet with 13 courses of 8" wood beveled siding. Five pipes and vents come through it.

How do you recommend I figure out exactly where to cut holes?
Are there any tricks or techniques to doing it better?
What's the best way to deal with felt paper?
Is there anything I should put between the exterior of the pipe the siding?

Thanks a lot!

 

Could you have picked an area with *more* obstructions to work around

For a small area like that I'd snap a chalk line for every course. Won't take long, and will let you adjust a bit if it makes life easier. Then you can measure from the end and the chalk line to mark the holes/notches etc...

You're going to want flashing around the window at least, if what's there isn't properly done and in good shape. Smaller penetrations are usually just caulked or foamed. I usually flash dryer vents. That large furnace exhaust (or whatever) should probably have a mounting block that is flashed.

Edit: would be a good time to replace that window while you are at it, looks like it's seen better days.

 

Hard to tell you exactly what to do. Its always best to remove as many penetration as possible... mark the locations, then use a hole saw to make the holes and slip the siding over. In some cases you may need to do make the hole but then if you cant slip it over you need to go around the penetration... slice the siding vertically (scarf joint if possible) then caulk the scarf joint. Allow at least 1/8 around penetrations for caulk.

Yes, use a WRB behind the siding, just seal it as best as you can, using flashing tape if needed.

If it makes it easier for you, you can also make mounting blocks first to surround some of your larger penetrations, then you put siding around the mounting block. Just depends on the situation and how you want to do it.

 

It rotten because it was installed to close to grade.
No way would I go with wood siding, just way to many future maintenance issues.
With any type of new siding I'd start with a stip of 1 X 6 PVC lumber first to get you the required 6" above grade for siding, Z molding then a kick out strip or your going with wood or Hardie lap, or J mould if you go with vinyl.
If you just have to have wood siding, your going to have to cut off those PVC pipes, make up some 1X wooden siding blocks and side up to them.