So it sounds like you have two questions:

1) can your siding be painted?

2) what to do about the yard

1) what is the siding made of? That will determine if/how it can be painted

2) what are your goals for the yard? Easy maintenance? Formal look? Wild look? Will you want a patio or some kind of formal entrance? I see you have a lot of Ideabooks on interiors. Browse for some exterior gardens and post those to see what style you like.

My neighbor who is Roundup adverse uses 30% strength vinegar and water mixture for killing weeds. Works well, smells like salad for a while after spraying. Lots of recipes for vinegar weedkiller online.

Thanks for the reply. I believe it's just vinyl siding. The house was built in the 80s and I believe it's the original. Yes, someone suggested we remove the big bush by the front windows of the house and extend a little porch out front, which I do really like that idea as the front is much more shaded than the back (back has zero shade). So I do like that idea so far...but that's as far as I've gotten. I will take your suggestion and look at the outdoor gardens. I do need something low maintenance as I am extremely amateur at this. I just want to keep all the wildflowers looking their best and basically keep up what is already there. I want it to look natural but well maintained, if that makes sense.

Congratulations on your first home. I think you have a lot to work with here, not sure your vibe but I've been loving the look of white stone/river rock and greenery. It's lower maintenance and adds a level of sophistication imo.

 With regards to the siding, not sure that can be painted or not. Unless it is wood in which case I know it definitely can be because we just did so.

I have used roundup against my better judgement and do not find it does much for perennial weeds my best line of defense is a really good ground cover. As for the rest I need to see the house and I agree we need to know what the siding is. Apparently you are still at the mercy of the HOA as to what you can do so get that figured out first or be ready to fight over every decision. I cannot tell you how much I hate HOAs . Usually landscaping like yours just needs some hard work to get it under control.As for the house itself if I am correct and those windows across the top are yours then the shutters do not belong and anymore help will only come with better pics of the house.

Pruning your shrubs would go a long way toward improving the appearance of the landscaping. I would tell your gardener to hand pull the weeds. Seriously, what did gardeners do before Round Up was invented?

Giving the perennial gardens a good weeding then mulching will prevent most weeds. Since you're not an avid gardener, I'd condense and reduce your perennial beds. Delete the planting at the corner of the driveway and reduce the planting around the lantern. Only keep the perennials that you especially like and group those thickly to cover the soil (this prevents future weeds).

You can paint vinyl siding, you just can't go darker than the existing color as it will absorb heat and damage the vinyl. Talk to someone at a paint store for advice.

I know stones are an appealing option, but keeping plant debris out of them is a major effort. Once dirt and debris get into them, small seedlings emerge even with a professional thickness barrier underneath. I know this all too well. I can see it happening with your river rocks.

You can tell an active gardener lived in the home at one time. If budget allows, I'd get a landscape designer out to do a plan that you can execute a piece at a time.

Thank you all so much for the info. We're going to start by painting the door and the shutters (unless the shutters are able to be removed, but think they've left marks) either a pink or green. Also, going to try to find a landscaper that can pull the weeds and will do the sheet weeding (sheet gardening? Not sure the correct name) with the cardboard on top around most of those side areas so we can try to start somewhat fresh -- not completely fresh because don't want to kill all of the wildflowers there. Thank you all so much. Hoping I can update with a beautiful garden or at least nice yard at some point!

1. Hire a gardener service who will pull weeds by hand to start off. Expect to pay for several hours of weeding to get caught up. Talk to them about what's a weed and what is a wildflower so they will not remove plants you like. Mystery plants can be clipped, put in a baggie, and taken to the local nursery for identification and advice. Have the gardeners do one bed completely first *while you are home* so you can see if they are doing what you expect. Or post online. There are many friendly experienced gardeners online.

2. In weekly or biweekly maintenance, they should also edge the driveway and sidewalk and the perennial beds. Be specific (print out a list) about what you expect so they can bid on the job appropriately.

3.The overgrown shrub next to the house can probably be pruned. Find out what it is. The customary height is about a foot below the window sill. Shrub branches are usually kept a foot away from the house to allow air circulation next to the house.

4. Pick up all the old yard decor items and put them on a table. Take a close look to see if you like each item and want to wash or repaint it. Pots and planters often need a good scrub, then new potting soil and new plants. July is a good month to clean up old pots before cooler days arrive in fall when you can plant bulbs. Old decor can be donated if you don't care for it.

We would be happy to identify any plant, wild or cultivated, over on the Name That Plant Forum https://www.gardenweb.com/discussions/namegal Give us a photo and tell us your location and we’ll do our best.

Here are some ideas:

I too would keep the siding and focus on a good power wash and step maintenance. Prune that bush by your window, don't be afraid to cut down by 1/3 (I would prob do this in the fall where I live). If there is a gardener friend in your family see if they can help you identify weeds, and then you can start by getting rid of them. You have a lot there...but much looks really good. I like Preen for keeping weeds down. In sum, I would start with an aggressive weeding/pruning and then see what you've got. If you had the money, a new door would be great. Those victoriana doors are just bleh, esp in a cool house like yours. Or maybe keep the door and just replace with clear glass.