Priority should be given to the structural and "living" requirements. This means roof, furnace, plumbing, electrical, etc.

Once those are dealt with (they are normally the big ticket items as well), you can start looking at upgrades such as windows/doors. While you are there, windows/doors often require some damage to either the drywall or to the outdoor cladding. If you are adding insulation to walls it can be a very good idea to have doors/windows/cladding/insulation done at the same time - because the damage that is done for the windows and doors often mean some form of 'upgrade' or repair.

These are your big ticket items. After that, you can decide which gives you more pleasure/investment and go from there. Landscaping is often done in fair weather and interior jobs (painting, retiling, etc) during foul weather. It all depends on where you live.

As Cancork said check the outside of structure first, interior remodeling for us is reserved for the wintertime. If you a have tree likes ours which by the looks of it is 200-300 years old, check for rotten old limbs (heavy ones) that may damage your roof and lop them off. BTW, Anybody need some kindling firewood?

Agree with updating the exterior first so in case there are any major weather proofing issues.