Disclosure: this post may contain affiliate links, which means I may make a commission if you decide to make a purchase through one of my links, at no cost to you.

About a week and a half ago, I was woken from a nap by the sound of a woodpecker kicking in my front door.

Kidding. I mean, he was making noise, and it was actually a pretty tiny hole, but it also happened to be taking place on the exterior of the house directly behind my headboard (which is also where the chimney is located). This tiny little woodpecker was eating a tiny little hole in my house. And as those of you who have ever had a home with wood siding knows, that sound is not a tiny problem.

In fact, it’s basically the equivalent of “Your house is going to fall down. Now.”

You see, woodpeckers only go where insects go. Insects only go where there is damaged or rotting wood. And since this house has seen its share of repair jobs to previously termite-infested areas, and is made of wood, I knew there was a very good chance that all of those things could be found in more than one spot somewhere on the exterior. Which leads to a great big welcome mat and blinking neon sign for new critters that want to be my roommate.

I had a pretty good idea that this might eventually happen, especially with blowing off these repairs for as long as I have. When I first moved in, there were a number of places where it appeared that the previous homeowner had done a handful of repair jobs and simply ignored a growing concern (which led to the aforementioned termite infestation that had to be dealt with before moving in).


A couple of years later, I had some minor repair jobs done by a family friend, but some were only half measures to keep the insurance company happy (obviously turning me into a pot versus the previous kettle’s shoddy jobs). The house was also painted around the same time (by the same family friend), which I continued to a certain degree.

house painting


It was slow-going, but it was really making the house look brighter and more cheerful. Painting and caulking does help keep things protected for a while, but I knew that it would only be a matter of time before I had to revisit the issue again, especially the chimney area (since the repairs were intended as more of a stopgap than a complete fix).


That, plus the fact that I’ve never quite had the balls to put myself up on a two-story ladder alone to finish painting some of the trim slowed things down a bit (my Dad actually fell off a roof and shattered his wrist once, and I’m pro-turning doorknobs).

So, I made the decision that this year was finally time to suck it up and get my home’s exterior addressed. If I’m honest with myself, my pushing this off has less to do with the stubborn notion that I can do it myself and has more to do with the fear of what it would cost to hire a pro to get it done right (certain things, like hiring someone to fix my home siding, aren’t as much of a DIY pride issue as, say, tiling my kitchen backsplash). And while I’m a pretty good saver who hates debt, I’m not the kind of person who is really eager to see my rainy day funds disappear. Even on rainy days when my siding really needs it.

I started the way I usually do these things—by asking my BFF. That led me to a site called Home Advisor, which led me to phone calls from several contractors in my area (and a lot of spam emails, so just a head’s up!). Most of contractors I found showed up (which is usually the first problem!), looked around the property, and gave me quotes that were UNDER the budget I’d allotted in my savings. And that’s what surprised me; all this time, I’d been scared of pursuing a more permanent fix for the exterior because I just assumed that it would be too costly to deal with “right now.” Only the numbers came back without a you’re-gonna-wanna-sit-down-for-this sticker on them. Maybe the repairs we were making made a difference after all.

new house pic

I had set aside more money than the estimates needed, but I’d already done the hard part of compartmentalizing that money in my mind for exterior improvements. So, it got me thinking… what other projects really need the pros but I’ve been too afraid to ask for? After all, if I’ve got the budget and I’m already prepared to spend it, so let’s see how far it can stretch, right?

Without hesitation, I knew my answer: the pine trees. All but one are in relatively good health, so it’s not really a falling over issue I’ve been worried about. But as pine trees are wont to do, the lower limbs shed as the tree grows taller. This leads to dead branches and limbs hitting my roof, getting tangled in Charlie’s outdoor leash, and general cleanup hassles.

The tree in the front yard is looking dangerous with a big gash in the middle, known as a “canker”. Obviously, this makes the tree more likely to split in this spot, which increases the risk of it crashing through my house (or someone else’s).

pitch canker pine tree

Also? There’s a shitload of pine needles. They blanket the roof, the back yard, the front yard, and cover everything in general brownness. They don’t let grass grow. They clog my gutters. They stain and discolor my patio. It takes multiple rounds every year to bag up and haul away (but I’ve found an easy way to clean up the front yard at least!). I’ve done some significant cleanup in both yards before to take out the lower limbs that I can reach on a ladder, but the majority of the root of the problem is much too tall for me to get to safely. Back to the web I went, and asked for a quote on doing some limb work to get to the biggest troublemakers.

And then, another surprise: that quote came in a lot lower than I expected, too (okay, the first one didn’t, but the rest of them did). So instead of limb work, I asked for additional quotes on removing the trees that were closest to the house. And after a little negotiation, out of the six total pine trees putting up a fight in my yard, I was going to be able to get five taken out and still fit my original budget!

In other words, this last week and a half has been somewhat surprising. In just a couple of weeks, I may no longer have a yard full of pine trees and a house exterior that’s repaired and painted enough to no longer embarrass my neighbors. And the welcome sign for nap-ruining critters will be taken down. Duh.

marking tree for removal

As the progress happens, I’ll be sure to keep you updated about what I learn along the way (the tree guys I’ve signed on with seem to be more than willing to share their knowledge about how to identify when a tree should be removed and other tips, so I’ll pass it along). I’m also writing up some tips about negotiating that proved to be effective for me.

Guys, I’m sofa king excited again. Can’t waitto show these updates!

Similar Posts

Leave a Reply

Comment Policy: I love comments, especially if they make me laugh. Feel free to let your words of wisdom and humor fly (there's no swear jar on this blog), but if you're overly spammy, rude, or just plain boring, you're just going to have to accept that your comment may not see the light of day. P.S. If you leave an affiliate or monetized link when making a comment on this site, such links might get overwritten by a plugin I have installed that uses my own internal tracking. See terms and disclosure page for more info! Thanks in advance. You rock.

This site uses Akismet to reduce spam. Learn how your comment data is processed.


  1. Very exciting! I am so excited to get our outside updating done this Spring. We are ready for the investment and thrilled to clean up and fix up. We had our trees trimmed and two removed late Fall of 14′. It was so stinkin’ fun to see the trees taken care of! Seriously, it just felt so good knowing I was taking care of them. And I have to laugh…do you think standing on a bucket and wearing flip flops is what the Safety Police would recommend? (Obviously, I am one!) You like to paint in heels, so this is for real or just an endorsement for the paint. We are on week three of no estimate after I called two weeks after our mtg! ARRRGGHHH! Please post those negotiation tips!

    1. Actually, it’s funny you pointed out that photo! Since this post was recapping progress made to the exterior, I’ve used old photos from past posts and that was from a sponsored one back in 2013. I really DID stand on that bucket to do some painting and thought, hey, this would make a funny shot! The paint was simply the paint I was using & I like to include the paint labels when doing projects (the #1 question of any DIY site is always which product people are using, so it helps to include them in photos).

      I am with ya on the safety though. I’m in the market to find some reliable shoes I can DIY in but are easy to slip on (always the reason why I navigate toward flip flops when I’m in a hurry).

  2. YAY! That’s exciting! Like you, there’s a lot of things that I DIY (I like to do it, plus the bonus is the cost savings). But, I know my limits. There’s several things that I want to hire out, but am afraid of the cost, so I’ve never looked into getting them done since I’m not ready (at least I thought I wasn’t) to pull the trigger. My other problem is that I work full-time so it’s hard to coordinate & get time off. Anyways, this is very encouraging! I need to make a list of what I want done and maybe at least get some quotes so I know I’m going to be dealing with and finally get some of that stuff done!
    Can’t wait to see more of your updates!

  3. Before we bought our house, I was so naive how much mess trees can make. We live on a relatively small property with only a couple shedding trees but man, they keep me busy! Along with all the other maintenance and a couple slow moving projects, we almost always fill our huge green waste and trash can with debris. I can’t justify paying for another one every month since there’s always plenty of other stuff to focus on. I’m just glad we don’t have any monster trees! The one a few houses down already gives our pool robot cleaner enough work as it is :) Congrats on getting rid of those suckers.

  4. Hi, I just came across your site, saw your current post and project, and thought I’d give you a helpful little tip. If you get pine sap stuck on your hands, spray them with PAM spray and rub it around a bit and then wash your hands. Works like a charm!
    I look forward to going back through your blog to see your whole progress, cheers!