Remodeling House- Where Do I Start? (Details Inside)?

My new home is a major "fixer-upper", and so far we aren't running into many problems remodeling this inside..but we haven't done a whole lot. I would like to get to the outside, now that it's warming up and I really dislike the curb appeal of the house. Here's the thing: I don't know... show more My new home is a major "fixer-upper", and so far we aren't running into many problems remodeling this inside..but we haven't done a whole lot. I would like to get to the outside, now that it's warming up and I really dislike the curb appeal of the house. Here's the thing: I don't know where to start!

One back room of the house had roof damage that was left unattended and caused the ceiling joists and boards to need to be replaced, as well as the roof (so basically it needs to be redone inside and out). It's a fairly large room, 10 x 20 or so, and since the house is smaller, I would like to get it repaired so that it is useable.

The windows in the house are not all proper windows, some are just the outer parts of storm windows (the single pain that goes behind most normal windows), and so therefor of course the house doesn't stay properly insulated NOR is it sound proof so I have to listen to the neighbor's dogs bark constantly and that's something I'd really like to change ASAP.

The siding on the house is dark dark brown cedar shake in front and dark dark brown wooden siding on the sides, so it's appeal is just gloomy and it will be replaced.

Here is my dilemma: I don't know what to do first. I plan on replacing the windows with as close to the same size as possible (unless some of the windows are custom, which I think only one may be), I want to put on a metal roof, and vinyl siding. Which do I do first? Is there any order that would be smarter? I mean..do I have to put windows in first before I side the house, due to trim and framing?
I just don't know what order to do things or where I should start. Please help. Any DIY handyman/handywoman help would be appreciated. I'm a fairly experienced DIYer and have the help of friends and family who have contractor/construction experience when it comes time to get the job done, so telling me to hire a contractor will not be appreciated. I really have to do this paycheck to paycheck and want to save where I can. This is a transition home, so I'm looking to do things in the most efficient way possible.
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