I've been in excavation for over 20 years, and from everything I've seen with hundreds of properties, proper drainage and grading gives the best ROI hands down. It's not sexy like a pool or fancy landscaping, but it protects everything else you invest in.
We had a client in Indianapolis who spent about $8,500 on regrading their yard and installing a French drain system. Within two years, they sold the property and the inspector's report showing zero water damage or foundation issues became a major selling point--they got $15K over asking because buyers felt confident the home was protected. Meanwhile, their neighbor had to drop their price $20K due to basement moisture problems.
The outdoor living benefit is immediate too. One homeowner told me they finally started using their backyard after we fixed their drainage--before that, it was a swampy mess half the year. No standing water means you can actually enjoy your property, your landscaping thrives instead of drowning, and you're not dealing with mosquitoes breeding in puddles.
From a pure numbers perspective, drainage work typically costs 50-70% less than fixing foundation damage, basement waterproofing, or landscape replacement from erosion. It's boring infrastructure work, but it's the foundation that makes every other outdoor investment actually last.