Siding and Windows..Is it Worth the cost

[Jared Baker]

Hello BP.

I'm continuing work on my triplex that I purchased 1 year ago.  I have 1 unit rented, 1 almost finished renovating, and 1 unit that I'm hoping to get started on in the next few months.  One thing I am considering doing is redoing the siding on the building.  Currently it is a particle board plank type siding.  Bottom boards are rotten and falling apart and the paint is de-laminated all over the place.  My current plan is to reside with vinyl which is definitely going to help with curb appeal and make it a maintenance free exterior for the most part.  My question is should I replace the windows as well?  All the windows are wood framed (look original) and there are atleast 2 (of 15) that are rotten and will need to be replaced when residing.  Should I go with the additional expense of replacing the windows as well?  Trying to balance the cost of this vs what it will do to the value of the property.  To give some numbers for the property:

Purchased for $155k
Current Rehab Costs $9k
Future Rehab Costs $3k
Replacement Siding $3k
Replacement Windows $5k
Rent $2100 per month

This is my first property and I'm learning quite a bit so I know the numbers aren't perfect but this has definitely been a good learning experience so far.  I haven't decided quite what to do with the place yet. I would like to keep it, but if I move I may sell it because I may be too far away to manage it.

Any thoughts are appreciated.