Just bought my second house and unlike the first I'm not going to let the maintenance and upgrades slide until 10 years later when I sold it I had to invest a lot of money in it. The difference with this second home is that I chose it, instead of it choosing me (a friend of mine was going through a divorce and needed to sell his rental properties) and I also am lot older and wiser let's hope.
Anyway this house (bungalow) was built in 1945 and has 700 square feet (single guy does not need more room) of liveable space (big open attic), it also has a much newer 3 car detached garage. The lot size is 70' Deep by 100' Long (corner) I also own the empty lot next to it that 100' Long by 140' Deep.
1st thing I have done is paint the interior with new modern looking colors, I also have plumed in the basement water and gas for my clothes washer and dryer.
Next I will replace the basement windows (old and drafty) with inexpensive vinyl ones that will keep the basement with fewer bugs and keep the heating bill lower than with the previous owner.
I will also seal the foundation walls and basement floor to keep the humidity out.
Update electric, install central air, renovate kitchen and small bathroom replace all windows with vinyl energy efficient ones. Create a master bedroom upstairs in attic with maybe a 1/2 a bathroom.
Lots of plans for the inside, as well as the outside yard needs some TLC and creativity.
Cheers and Good Luck to us All,