Roof first, then electrical and plumbing, then windows if they need replacing, walls and floor.

And that could mean an inspector would make you upgrade that bedroom to arc-fault breakers and mandate proper egress windows.  

For instance, if the property has a significant amount of 'deferred maintenance', you know, broken windows, worn roof, or a missing central air unit, it won't be eligible for conventional financing.... that just means you'll have a hard time getting a loan for it.  

Major repair of a tile roof is about $30,000.Keep the old wood frame windows if you can.

You can then make generalizations, for instance, a 1920's construction home may typically warrant new windows when they've never been updated.  

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Okay, got a new Toshiba Note Book, 5 days ago, finished installing Windows 10, seemed that was the answer to Slooooooooooooow processing on BP, and nowThe scroll hesitates jerky, slow, no response using the down arrows, page changes are slower.A banner pops up, "Shockwave plug in not responding" by the time I can get to the button to stop it, it's gone. 

Not totally, but, it needs siding, roof, kitchen, bath remodel, windows, and landscaping plus finish work.

- It amazes me that someone would throw money out the window like that.

Nasty issue is the curved glass windows are impossible to replace.