You have a lot of changes planned. I don't see shakes on the second story. But changing the siding and the windows will make a big difference. Good luck!

Do the windows need replacement or do you just find them unattractive? To the right of the door I see two windows. Are they in the same room?

It looks to me like what you need most is good landscaping.

It's not terribly inviting. Do you just walk on the grass to get to it? An entry path and some landscaping would help. An entry roof would keep rain off you when entering, and provide some focus to the facade.

I see no shakes and I personally would not do shakes. You need a walkway to the front door I would add a porch and then if the windows are bad change them to no grids and do just simple siding in a color you like and then get to work on the landscaping. I would look at aporch all across the front to make it look more inviting

In agreement with the porch. Need an enlarged entry pad and add a walk to wherever the parking place is. Need some simple landscaping, with beds deep enough to hold shrubs.

Plus new modern outside lighting

What program are you using? Love this!

I use photo editor

Do you even use this front entry?..and how practical is it to have landscaping that needs maintenance?..will you do that yourself ?...do you just come for weekends and vacations...summers?..all these things should figure in to your plan..