Cost of anything you do with/to your home should not be measured merely by the $ sign. You need to take into account durability, energy efficiency, fire retardation, manufacturing/recycling issues/abilities and other things as well.
PVC (vinyl) siding isn't really all that and a bag of chips. It is actually a deadly thing in its manufacture and, lord forbid, should your house catch fire. We won't even discuss what happens when the house is either remodeled by someone else or finally must come down to make way for a new neighborhood, or store, or what ever and the material ends up in land fill or “recycled” where once again it becomes a nasty, dangerous toxin. To appreciate the problems of PVC I provide this link:
http://www.turnertoys.com/pvc9printable.htm and this one:
http://www.ineed2know.org/VinylSiding.htmSo you have the monetary costs, but then you have the ecological/environmental costs to consider as well.
The safest and longest lasting is Aluminum - lasts longer than steel, is safer when it comes to manufacture and reclaiming, if the house catches fire it will not burn. Steel keeps on rusting, especially on the interior in humid areas like Ohio, aluminum does rust (oxides), however once it gets a protective oxide covering it stops rusting.
As an aside, vinyl siding is more likely to catch fire if your neighbor’s house goes up in a blaze of glory, If not actually catch on fire, then melt/soften/warp. Metals are fire resistant and less likely to cost you when it comes to fire. Vinyl also tends to warm/crack/come loose in regions where there are hot summers and cold winters more often than in mild climates.
It is possible that Aluminum will last longer, meaning you will get more bang for your buck.
Both aluminum and vinyl are paint able these days – or better, there are paints which are designed for once unpaintable surfaces – that and the popular use of spray painting instead of brush can increase the life of either of those two materials while still affording the owner the chance to change the look of the house with different colors.
Windows:
Double paned (Doubled glazed) is the best option. It provides the optimum return on energy efficiency to initial lay out of cost. Although triple paned windows exist, they do not actually perform much better than double pane. This is due to the properties of glass (conductivity and insulative values).
If cost is a problem, you can break this down, instead of switching out all of the windows at the same time, you can switch out a few at a time, spreading the cost over time. Usually this is done by addressing the northern exposure (in northern areas where cold is the biggest problem) or the East/Western exposure where heat gain is the issue in the first year.
I would recommend doing the windows before the siding – you might (might) decide that you want to enlarge a window opening, or add a window – that would result in your new siding being subject to reconstruction which might cost you more.
Not only does the cost of material have to be figured (the windows and the siding) but also the labor costs. A home owner can (if they have the skills and tools) replace their own windows at a fraction of the cost of hiring a glazier to come out and do it – in that case you could (in theory) spend more money on the siding and/or the windows.
Labor costs range greatly from area to area, contractor to contractor. That will eat up half if not more of your budget for the windows and siding.