Need suggestions with existing wood siding

I am a new homeowner and don't know too much about siding. I want to know what would you do if you were in my situation.

Siding on my house is wood shingles (I think its also called as cedar shingles) which is falling apart, literally. As you can see from the pictures, a lot of shingles are warped and there are places where nails have come lose and shingles are falling out. if I were to guess, about 40% of shingles will need to be replaced i.e. only 60% of shingles are good.

I did some research and found that wood shingles siding is expensive and better looking than vinyl. Now I have couple of options. Either get the large missing shingles patches fixed and get the house painted. Or get it replaced with vinyl siding. is there any other option that I missed?

I know this should really be my decision but i really would like to know what you think and would do if this was your home.

Some of the things that will help you make a decision: I plan to live here long term. Budget is available only for vinyl siding, House is located in Long Island, NY.

 

I would replace all of the shingles. It goes pretty quickly with a finishing nail gun & a couple workers. Vinyl siding is too flammable, for my liking.

 

I prefer the look of the shingles over vinyl siding BUT wood siding [any type] will always require periodic painting while vinyl only needs to be cleaned every so often.

 

James Hardie - Choose 100% Hardie™ - Products | HardieShingle Siding