IMO the trees need to go they over power the house and are also way too close to the house and you already have experienced the issues with huge trees .IMO a bit MCM ranch so remove all the shutters . I would say that once you remove those trees the porch paint will last a lot longer but you need to use proper paint and really good prep and making sure the porch is totally dry and then no walking on it for 72 hrs that gives porch paint a chance to cure . This is my fave for MCM ranch landscpaing and I think it is great for inspiration if you want to go that direction. Can you tell us a bit about your style inside it just helps with ideas no rule says the inside and outside have to be the same style.You will need to address the drainage issue the water is still too close to the house coming off the roof IMO. I always like a walkway from the street to the front door , for landscaping I would start with that .

Hi Patricia, thanks so much for your thoughts. I agree with you that we should think about removing those trees. Due to the damaged sidewalk. Though once we do that, the porch will get more sun, as the trees do help to block some of it, and by late afternoon the porch gets full sun and streams in through our front door window. So I’m not sure removing the trees will help the porch paint. It is a concrete porch which has been painted. But there’s always a lot of pine needles that fall on it that I’m always clearing off. Feels like I’m always dealing with pine needles…lol.
There are rain gutters going all around the house along with rain spout extenders. But anything else we can do to help with drainage would be a plus.
The walkway from the street is an interesting idea. I’ve never paid much mind to the walkway, so I looked around our neighborhood and some neighboring communities for more inspiration. I noticed that most have a walkway coming off the driveway, a walkway from the street is not common around here.
The inside of the house is still a work in process, it’s going towards a coastal vibe.

I hate pine needles. All they seem to be good for is mulching strawberries. If I were allergic to pine, I would be considering selling and moving away from them. Is this to be your "forever" home? If your issue requiring a cane or scooter declines further, the needles and general upkeep of the home may become an even bigger burden for you. Think things through with a view to the situation 5 years down the road, and make long term decisions if you have the budget to do so. In my area those trees would cost about $300 each to remove. You could finish up the interior updates and get it on the market with that money.

It sounds like the trees nearest the house at least, are causing more damage and maintenance issues than any benefit they provide.

Since you’re considering a carport, get a landscape architect to also help figure out an overhead solution for the front door and porch area. I’d be thinking about a pergola or more solid roof system tied in to greatly reduce the pine needle litter, sun and allergy issues and they can help with new hardscaping to fix the damaged areas and address your mobility issues. They can take your whole property into consideration, for example, maybe the mobility issue is easier solved by using a different entrance which will also help curb appeal.

These pine needles aren’t my favorite thing here either @decoenthusiaste. We are always cleaning them up and I have definitely thought about moving to be away from them. And tbh I’m not sure if this will be our forever home or not but I am trying to think and plan for the future. As for the trees maybe tree removal prices differ, but for the trees we have, we’ve been quoted between $1000-$1200 per tree. Which is a significant amount of money. I wouldn’t mind paying $300 per tree. We still have more things to do, like grade the backyard due to drainage issues and do some sort of deck/patio. We’ve installed a sump pump and that’s helped, but before installing any sort of deck we need to get the backyard grated first. So I guess it’s also figuring out the proper order of completing these things.
(i.e. We wouldn’t want to install/repair driveway and then have excavators trampling back and forth over them tearing it up.)

Hi @JT7abcz, thanks so much for your ideas. I like the idea of contacting a landscape architect and will definitely give that some thought.