siding or investment?

[Mitchell Litam]

I am currently house hacking my house and it is a duplex. My house is not 100 years old and has wood siding on it.

I replaced a couple of pieces from dry rot 6 months ago and now I have a couple more pieces. Easy fix. I just got an estimate for $14k to side the whole house but the guy said I should do windows first if I was thinking about siding the house. 

I plan to move out and rent this house in about a year. My questions is should I invest the $14k in the house for worry free maintaince when I move out or should I use the 14k on my next property? Also the windows are old but how much does a tenant really care about the outside and windows? They wont pay $100-200 more in rent cause I got new siding and new windows will they?

What would you guys think would be the best move?

Thanks for all your input.