Making the sought inspections is not very difficult as you think.
It is neither expensive and the scope is to detect damage and repair it while you still can.
Here are the components you should be looking at and the particular problems that they might have.
Maintenance Tips:

1. Loose Siding - Siding that has problems and has fallen out of its places.
   Siding is made to stay in place by interlocking each piece.
   Sometimes, some of the pieces can fall out.
   If you find a lost siding then you should put it back in place.
   
2. Siding with Physical damage - Water can penetrate into the house through a broken siding.
   Make sure you repair it buy another one to put in place.
   If you are unable to repair of the damage is too extensive, then you should not do the reparation yourself.
   Hire a professional or a team to conduct reparations.
   
3. Clear any objects that are near the siding or touch it as they might prove dangerous when they freeze.
   Make sure you remove any vegetation that is leaning towards the siding for the above mentioned reasons.
   
4. You should try to re-caulk any seam.
   Look for zones where sidings meet each other as when two walls meet or a roof slope meets the siding.
   You should also look for missing caulking.
   Caulking has many benefits when dealing with extreme temperature, just so you should know.
   
5. Weather stripping keeps the cold away from your home and helps maintain temperature in your house.
   See if you miss some stripping then you should buy one as they are quite cheap and easy to install.
   You do not really need to hire someone to do it as anyone can do it and it can potentially save you hundreds.
   
6. Watch out for soffits that are unsecured or broken as they can cause lots of problems.
   For example, you might end with snow in your attic and you could even find mice or birds there.
   
7. Make sure the fascia is well tied as the winds could disintegrate them if it is heavier.
   You could even try to fix it in place by using some nails or other things like that.
   

In general, these are the things you should be respecting when maintaining your house.
A properly maintained house could save you thousands of dollars during winter, so make sure you act while you still can because it can make a difference.