Six Land Buying Mistakes We Almost Made

Now that we are a year and a half into our journey towards building our debt-free home, the process of choosing our land feels far in the past. However, we recently got to thinking about the long, unexpectedly complicated journey we went on to secure the site of our homestead and we now have enough distance from the experience that we wanted to share what we learned with you.

In many ways, buying rural property is nothing like buying a house in the city, and the process if filled with unique challenges that can stymie buyers if they don’t know what to expect.

If you’re in the market for rural land or simply want to know more about the process, please take a look at these mistakes we almost made (or could have made) when picking our property!

There are many more factors to consider than just these below, of course… maybe we’ll create a comprehensive guide one day but until then…!

Land Buying Mistakes We Could Have Made

1. Limit the number of steep hills between you and the rest of the world.

Going up and down steep hills gets really tricky, especially in northern climates that experience lots of snow and ice.

We looked at some amazing properties with super steep driveways and wound up turning them down, which we’re glad we did because they would have added a lot of unnecessary complications to our life, especially when it comes to towing water up hill!

2. Avoid overly muddy roads.

Even great dirt roads turn into a mucky, muddy mess in bad weather, so while the idea of living at the end of a dirt road may sound romantic, it can be a major hassle during part of the year.

At the very least, try to research who maintains the roads near you so that you know who to call if it becomes undrivable in wet conditions.


3. Watch out for bridges.

In our area, bridges often get flooded in water and buried in snow.

One even gave way completely last year, and it’s probably not going to be replaced anytime soon.

If you choose to live on property on the wrong side of a flimsy bridge, you might be in trouble!


4. Beautiful trees become roadblocks during a windstorm.

Those beautiful old trees that were a selling point for your property? A major windstorm might knock them down (like our epic windstorm of 2015), so you need to think carefully about whether you’d be okay if this happened.

As a side note, always keep a chainsaw handy for little emergencies like this!

5. Where are the railroads?

If frequent trains keep cutting across your path on your way home, you can expect to sit for 20 minutes or longer waiting for your path to clear.

Also, trains are loud- even if you live far away from them. The acoustics of rural land can really magnify noise sometimes.

In fact, we almost bought the perfect property with a cute onsite cabin, but changed our mind when we heard an incredibly loud train rumble through that night.

6. Visit a potential property multiple times.

In fact, it’s best to always go back and visit a property at least twice so that you really know what it feels like.

A piece of land that looks gorgeous and dreamy by day might be a disaster as soon as a train comes by that night.

It’s also a good idea to make sure to visit it during different seasons and different times of the day, so long as you don’t think it will be bought first.

7. Remember, there’s no such thing as the perfect property.

There won’t be a single place you find that fits every requirement on your list, and that’s okay. Keep in mind that while you’re shopping for your dream property, the place you wind up with is bound to have a few flaws.

Make sure you take your time in the search process to truly find some place you love, even if it doesn’t have every requirement on your list.

And there you have it- seven tips for buying rural land that we easily could have missed.

There are many, many tips for buying rural property… what are some you feel you could have missed or learned from experience? We’d love to hear them below in the comments.

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I am an aspiring homesteader on a journey to become self-sustainable and free. In my past, I've worked corporate jobs to make ends meet and get ahead a little; it didn't make me happy or confident in my future. Since taking the leap to self-employment and living a more simple life, my happiness levels have increased greatly and I've never felt more alive. I finally understand what I want in life and how to get there, and that is what this blog is all about.


  1. Gamma & Delta says

    Some really great insights and tips here. Re: #5 As a die-hard railfan ever since my grandmother used to take me down to the New York Central railroad depot in my stroller in the late 1940s to watch the trains arrive and depart, that property with the cute cabin would have wound up high on my list. :-)

    Oops, typo in the second paragraph: “…and the process if [IS] filled with unique challenges…”

    Very interesting, inspiring and entertaining blog and YouTube channel (although I’m spending way too much time watching all the videos from the beginning). But, what the heck, our strawbale home is finished (well, it will never be really finished) and we just replaced the “temporary” roofing after 15 years with a permanent solution so I can justify the break.

    Thanks for letting us ride along. We wish all the best for you two on your adventure.

  2. Heidi Blalack says

    I’ve been dreaming of my own property for years and some of your tips are thing’s I hadn’t thought of yet so thanks so much for this post.

  3. says

    Great tips! Number 6 was a big one for us! We started looking at our property in the later winter through early spring. We’d stop by after a big rain storm to see the height of the creek and where the water pooled. I’m so glad we did. It helped changed some of our plans and layouts for the property!

    I recently wrote about 6 must do things when looking at a property to investigate. Your tips are totally different and equally as great! Thanks!

  4. John Gritman says


    Speaking of land selection, I was looking at the land behind your foundation and the soils in the bank you opened up to put your foundation in. I was pleased to see all the rebar you used. In this part of Ohio we tend only to use rebar in the corners. But then I am not at all subject to a mud slide; it looks like you are. When you back-fill the foundation, I would first have an engineer look at that soil and recommend a plan for stabilizing the hill side unless you are really close to the top.

    And I would make good friends with your neighbor with a tractor. Not now, but in two years you will want to do something with the land that is in front of your home. I would disc it and then run over it with a device I have seen. It is a flat blade of steel about 5/16″ thick which lays flat on the ground. To it is connected some HEAVY chain link fencing of equal width and at the back is an L shaped piece of steel securely fastened to the chain link fence. The front blade of steel is connected to the tractor with chain. Move the tractor forward and the soil that has been prepped with a disc goes over the first bar, the soil dropped through but the rocks don’t. The accumulate by the back bar. You have to back up to dump the rocks and then use your back-hoe bucket to remove them. We called this a rock-hound when I ran one in NJ 55 years ago. Then go back over the whole thing with a field rake or use the tool you’ve built in a different direction. Then plant grasses or wild flowers.

    I did this for a whole summer. Not hard, the back hoe or tractor with a bucket does all the work. You just have to be careful where you stop and turn. The weight of the backhoe will definitely compact the soil.

    The second problem is fire. If I am not mistaken the LA airport finally brought in some goats to clear the underbrush in the nearby hills, reducing the chances for fire. But that is something to discuss with the local fire people.

    My mistake in buying my last house was flooding. I wasn’t in a flood plain but I had a drainage ditch across the front of my property and running 200′ down the side. No problem or so I thought! The basement was dry and smelled clean and fresh. Then came 2003 we had a full week of heavy rain and then 7″ in 90 minutes. That did it! My super dry basement became a 2′ deep swimming pool 28′ wide by 76′ long in 15 minutes. The force of the water was so strong it moved a bucket of 12 horseshoes and stakes from one end to the other! I had both flood insurance and back-up insurance for the sump. And for some reason, God must have guided me to built my 8 large shelving units so the bottom of the bottom shelf was 2′ above the floor. So watching you with your housing drains was a great reminder!

    Keep up the teaching and the absolutely wonderful way you work together.

    May God shower you with His blessings.

  5. KrisZ says

    Kudos to you two for identifying and going after your dream at an early age.

    I’ve watched many episodes on your You Tube channel, but I missed how you guys are learning to do all that you do. I mean I’ve caught a few hints of talking to people for advice and learning from the internet, but you two seem to have more knowledge and experience than that. If it’s just an illusion, great job at it, but I sense there’s more to it. I apparently missed it. :)

  6. Michael Wier says

    You two are awesome! You have inspired me!
    For the last 10 or 15 years I have toyed with the idea of doing just as you are now, and have decided to do it. Although I do have have some loose ends that need to be tied and some financial obligations that need to be taken care of, I am saving as much as I can and looking for land.

    • Jesse says

      Everyone’s journey is unique. Don’t rush the journey, it’s not a destination and it has no end. Enjoy the process, focus on discipline and find joy in what you’re accomplishing even if it is seemingly small. As they say, the way to eat an elephant is one bit at a time. Thankfully elephants don’t have much interest in eating us. 😉 Cheers!

  7. Michael Wier says

    You two are awesome! You have inspired me!
    For the past 10 or 15 years I have toyed with the idea of doing just what you two are doing, and I have decided to go ahead and do it. Although I do have some loose ends that need to be tied and some financial obligations that need to be taken care of, I am saving what I an and looking for land. I wish there was some way to contact you directly…I’d shake your hands and buy you dinner! But until then keep up the good work!

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