Your house id nothing like any of the pics you posted. IMO the first thing is to get new windows without grids to modernize the house , remove all the growth from in front to be able to see the house.Right now I have no idea.

thanks for posting the photos of your charming home. much of its beauty is in its timeless simplicity, plus the darling bricabrac eves trim. it would make me smile to walk up to your front door every day. hope you feel the same. of your choices, Judy gs photo, or your Madison photo, reinforce the charm and simplicity. pick what makes you smile. ... and fits your budget for the garage, which isn't really visible from the front.

OP, sorry for potentially derailing your thread but I have a question I really wanted to ask for a while. I have a disclaimer first. I do not have any education in architecture and I am not a visual artist of any kind so I do not have trained eye for those things. Here is the question: why in order to have well designed and attractive house we need to hide garage doors ( and televisions, and refrigerators, etc.). Why "there is nothing attractive about garage doors"? I get it if you are building house that recreates architectural style from an era when those things did not exists. But for more modern styles, what's wrong with them? For example, I find this house attractive and garage (doors) do not take away from that for me: https://blog.scoutandnimble.com/blog/home-reveal-mixed-mod-part-ii What am I missing?

when I buy houses I get every contractor there is out to inspect the critical elements, someone mentioned above HVAC, roof, septic if applicable - to cover the big stuff... if I think aesthetic work needs doing I get a contractor out (usually your realtor knows at least one) and get an idea for costs from them. I then use that info to decide whether I think the aesthetic updates make sense vs the purchase price or you if they're even in my budget at all. if not then I either have to live with things or work around them or walk away. If this is going to be your forever home you can do it over time but plan on big bucks for the columns and the kitchen. professional painters are big bucks too.