Before you do anything find out what is under that siding.There is a possibility you may have asbestos siding, trust me you don't want get involved in removing that.Okay so if its cedar shingles or clap boards. What condition are they in. There is a chance that the reason the house was sided is because the siding had reached the end of its useful life. Okay so its cedar shingles or clap boards. You will be faced with the unenviable task of scrapping and filling a myriad of nail holes.
You may be much better served by leaving it and adding some newer siding in certain places as accents. The types of siding today are mind boggling, some of you would swear it is real wood.Check out Harvey Industries or some one similar not the box stores.
Finally vinyl can be painted. A good power washing and some quality primer and your all set.
One other issue, what kind of value will a project like this bring. Your house is only worth what the others are in the neighborhood.

These are all great questions. One thing I know is there is no asbestos. Thats one problem out of the way. The house was in excellent condition in 1960 (I have photos and know the woman who lived here then, so thats one other thing that is on the up side. The house was vinylized in about 1970. One of my concerns is that the vinyl is preventing moisture from properly escaping from the house, thereby rotting it from the inside. All of the non-masonry houses on this block are painted wood and the wood is in pretty darned good condition. that doesnt mean mine is, but they all have been exposed to the same elements for the same length of time and were all built within a few years of one another.

One thing I know is that the back porch, which was enclosed in about 1948, had vinyl that we removed to the old wood siding and it was, of course, in excellent condition, so I am hopeful that the rest of the house is in at least good condition and wont need significant repairs or stripping. If it is, well, we can always re-side it. One thing I read about painting Vinyl is that dark colors will make it warp.

Thanks for mentioning the value question - my house is only as valuable as the neighborhood. Sometimes I do tend to get carried away and forget about location - isnt it sad so many wonderful old houses are in less than perfect neighborhoods. Thankfully, all the neighbors here are significantly improving their property so were kind of hopeful at the least well make our neighborhood into a more desirable place to live.

Did you ever get an answer or proceed? I would like to do the same but one side at a time? Any advice?