Joys of owning a home

So Matt and I LOVE our new home.  Our favorite of the three we have owned.  This house though when we started having winter conditions problems started appearing :/ really frustrating I tell ya.  The first sign was a frozen pipe to just the basement toilet thankfully Matt has found the remedy for that :) Then there was a leaking window upstairs, but after drying up the mess the leaking stopped.  This happened right after the first snowstorm of the season.  So we didn't think much of it (I checked it periodically to see if there was a leak, but there wasn't).

This last storm that came with freezing rain followed by 4-5 inches of fluffy stuff resurfaced the problem.  The night the storm hit I was awoken by dripping water and yes the window was leaking once again and hasn't stopped.  I have found where the water is dripping (from the roof under the gutter) and understand why it is dripping through the window (bad seal/installation of the window) into the house (not to excited about how much it will cost when we see the full damage).  Then today the basement window below the second story window started leaking and since that window is more accessible I found it is the same as the upper window.

Now we just need to figure why the roof is leaking: do we need a new roof, is there some air thing happening in the attic caused by vents like the internet suggests, or is is just ice building up between the gutter and roof and melting down the house and causing ice to form on the window and melting and ruining the seal.

Is it bad that I stress about things like this? I feel that I should because if I don't when will it be fixed.  It is hard to fix things in the winter too ugh and the official day of winter starts tomorrow.

I am hoping by venting here that I will be able to level my emotions out and have a rational head on. I am frugal and when problems occur I get stressed on the money side of things.  I know that we are still safe and that we will survive, but how much is it going to cost to fix.  The older I get I am surprised more and more by how the level of our finances affects me.

Sorry for another vent post, but I really want to fix this problem, but I only have the resource of the internet and the prayer for patience to wait for help.