The Happy Story of The Worst Vacation Ever

by |

Last week I was on vacation in the idyllic little lake in New Hampshire called Lake Ossipee.

It was an incredible vacation with some hiking, shopping, swimming and just kicking back and relaxing with the family for a full week.

It’s great to get away and give your brain a little rest and your body time to rejuvenate. And fortunately for me, things are going so well right now; it was a particularly restful and relaxing vacation, knowing that my newly assembled team was taking care of things back home.

Some people would think I was crazy for going on vacation in the middle of four rehabs and a modular home build – something which I’d never done before.

Maybe so.

But for me, I thought it was the perfect time to get away. After all, I had a great team of people that I had painstakingly assembled over the course of the last several years who I have the utmost confidence in and to top it all off, despite a lot going on, things were going really well.

Plus, I thought, “What could possibly go wrong that I haven’t been able to handle before?”

After all, two years prior at the exact same vacation spot, I had lived through one of the most stressful and trying times of my real estate investing career. So this time, I felt confident that I could take what I thought was a well-deserved break because as bad as that week was…it had not in fact, killed me.

The 20 Best Books for Aspiring Real Estate Investors!

Here at BiggerPockets, we believe that self-education is one of the most critical parts of long-term success, in business and in life, of course. This list, compiled by the real estate experts at BiggerPockets, contains 20 of the best books to help you jumpstart your real estate career.

Click Here For Your Free eBook!

Contrast and Strength: The Power of How Much Difference Two Years Makes

If you’ve been a reader here at BiggerPockets for any length of time, you probably know that although real estate investing may look easy on TV, it’s anything but. Real estate investing is filled with many triumphs that get you so high…but unfortunately, it has its fair share of lowest of the lows as well.

In some strange way, the not so good times actually happen for a reason and not only do they make you a better business person but they also makes you enjoy the good times far more.

Think about it: if everything always went well for you, you’d never have any contrast – and contrast helps you to appreciate the good times far more thoroughly. Some may disagree with me on that but I absolutely believe it to be true. The bad times do happen for a reason.

And the last time I was vacationing in the very same spot in New Hampshire two years ago is when one of the worst of these times smacked me right between the eyes and sent me reeling for what for me personally, was the worst vacation I had ever had.

How Much Difference Two Years Makes

As I took my family to Lake Ossipee two summers ago, I knew that going on a planned family vacation was probably not the wisest things to do. At the time, I was facing some pretty big challenges in my business on two specific issues that were far from being resolved.

It wasn’t easy leaving the business while this was going on but I always believed in taking at least one vacation every year with my family regardless of anything. I guess I can give credit to my parents who always took us on vacation every year and in most cases it was north to New Hampshire to try to escape the hot muggy days in suburban Boston. I’ll always cherish those drives north and the fun times we had as a family.

On this trip however, I had just started one of the largest rehab project I had ever taken on. At over $100,000 and counting in cost, we had run into multiple cost overruns – and although I had a good team doing the rehab, I wasn’t at the point where I could just leave town and let them run the show.

Prior to leaving, I had done all my due diligence on the contractor I was using and although I had never used him on a project before, I really thought everything would be fine. A few weeks into the project – and two days prior to my departure on vacation, things changed fast.

That morning the town had placed a big white and red stop work order on the front door of the home we were rehabbing.

All work on this massive rehab stopped immediately. This was a first for me.

I immediately panicked and thought; “Should I cancel our vacation to deal with this? Should I send my wife and kids without me? What the heck should I do?”

I decided to go and although it was a tough decision, I was ultimately glad I did.

New Inspectors and Town Officials…New Challenges

As it turned out, there was a new inspector in town – one who I had never met and he didn’t know me form Adam. If the old inspector was still in charge, I may have been able to work out the issue with far less pain because of my good prior track record with the town. But because I had no history with him at all, this was not the case.

After I told everyone I was not going to let this spoil my vacation, a good friend of mine volunteered to represent me and offered to deal with the inspector and contractor and attend all the meetings while I was gone. He and I talked every day on the phone while I was on vacation just to make sure things got resolved.

Still to this day I second guess my decision of not sticking around to deal with this firsthand. But I had committed to my family to go on vacation and I didn’t want to let them down. Maybe subconsciously, I thought that if I could escape and not deal with it, that somehow, miraculously while I was vacationing it would all work itself out.

Not a chance!

Issues With The Flip

While this whole stop work order debacle was going on, I had another situation going on that was getting worse and worse each day. This situation, although it was made far more complicated than it ever should have been by certain parties, simmered up to a boil when I was away as well.

I had purchased another house at auction and for what should have been a simple clearing of the title, but boiled over into a politically-fueled denial of title caused by the Town Administrator and later the Board of Selectmen.

To simplify a complicated situation, there was some old town politics between a worker of mine who was a former selectwoman and another former selectwoman which caused this all to occur. And because the first selectwoman had previously worked for me, I became the target. The former selectwoman – who was still heavily involved in the town boards – got wind of my request and turned my request for title on this property into a public platform. A platform to lambaste investors in real estate who are “taking advantage of” the citizenry of the town.

Fair enough. If you’re a real estate investor long enough, you’ll eventually get this sort of treatment. I get it.

Of course, the people who accuse legitimate real estate investors of wrongdoing almost always fail to see the good we all do by cleaning up towns, buying distressed homes and increasing the real estate tax base for the town – not to mention putting to work the dozens of subcontractors and workers who help in part to boost the local economy.

Nope. People like her only see us taking advantage of the people who are down and out – exploiting them for our own greed.

I only wish that she called me or met with me to get to know me and my business a little before she went and made a public spectacle of me and my business.

Moral Dilemmas In House Flipping

The problem was I had sold the house to a young couple and their child – but because of this title issue, the formal sale had turned into eighteen months of pure hell for me. I told the couple I would do whatever I could to clear this up – but there was no way I could have imagined it would have taken 18 months and over $30,000 of my own money to deal with it.

After realizing how complicated the situation had become, I told them the best thing would be for me to sell them another house I had or have someone else move in and not have to wait for me to get this whole thing cleared up. They told me they loved the house and considered it home already and didn’t want another house.

The easiest thing for me to do would have been to just rent the house out at $1,700 a month which would just about cover my monthly costs and I’d spend all the time I needed to clear the title while I collected rent.

But this situation was different. The couple asked me if they could rent the house from me at the same monthly rate of their mortgage instead.

Great…or so I thought.

Because they qualified for a USDA affordable loan program, their monthly mortgage on the property was just north of $780leaving me $1,000 a month in the hole.

Responsibility and Keeping Your Word As An Investor

Although I’d be taking a hard hit on the monthly financing and carrying costs, I felt partially responsible for their predicament. So after much internal debate, I told them I’d do it – but I couldn’t promise how long it would take and couldn’t guarantee eventual ownership to them. What I could promise is I would do whatever I could and fight to the end to get them their home.

I just didn’t realize that when I told them that it was going to take me as long to resolve nor would it cost me as much as it did.

However, I had given them my word and I was going to stick to it.

So the critical moment – when I was to appear before the review board to resolve this whole thing – just so happened to be the very same week of my vacation in New Hampshire…

My attorney insisted that he could handle it all on his own and that I should go on my vacation and not let my family down. “You just relax and I’ll take care of it”, he said.

Little did we know that this was slated to be a public hearing packed with people – many of whom were against me and the real estate investment community in general. When my attorney arrived at the meeting, much to his surprise the room was packed with people… he had unwittingly walked into a public witch-hunt of sorts…and he and I were the one at the stake.

Needless to say, things did not go well that night…

Real Estate Investing Is In Fact…HARD

When you write in many posts that “house flipping is hard” or “real estate investing isn’t easy”, these are the situations people refer to. You simply can’t make this stuff up.  Afterwards, I second guessed myself again and was kicking myself that I should have been there to defend myself from the haters.

Try to imagine the stress and feeling I had going on in my head while trying to enjoy a family vacation. Suffice to say, that vacation was anything but relaxing. I felt stressed out the entire week. It was the worst vacation I had ever taken…or so I thought.

But although it all seemed like the end of the world back then, I did in fact live through it. And thinking about it now, that week of hell did make me stronger – as well as make me to appreciate what I have now.

No Defeat Is Final

“Never confuse a single defeat for final defeat”

– F. Scott Fitzgerald

So we ended up back at the same vacation home two years later. This time however, we took our weeks’ vacation under a whole new set of circumstances – but these were all good circumstances.

My business has never been better, I have great people working for me, I’m having more fun now than I ever have, I’m doing things I’ve never done before, everything is going great. And what’s even better is that now I realize that no matter what happens, I know I can bounce back from it – no matter how desperate the situation may seem at the time.

Call it experience, call it seasoning, call it just knowing things will work out – whatever you call it, I think to have that frame of mind – you have to have been through it, experienced it first hand and learned from it.

I know I did.

Relaxing Vacation…At Last

This vacation was so much the same and so much different. The same being we did a lot of the same activities the first time including shopping (girls love to shop) at the outlet stores, heading up to North Conway and visiting Zeb’s the famous general store, going to the beach and spending time out on the pontoon boat and tubing on the lake.

The difference is that this time, I left my business with no real worries at all. Because of my bad experiences prior, I do my best to not repeat them and so far things are working out extremely well. I also have better systems and better people in place to take care of things.

Is that any guarantee I won’t face difficult situations again? No way. But I can tell you there will be less of them for sure and most likely no repeats.

This past week, as we were all sitting around the dinner table enjoying our time together in the very same place, the very same house we had all been two years prior when all this was going on, I reminisced to my wife Christine about the very different circumstances two years prior.

We laughed a bit and my kids asked us what we were laughing about. I then proceeded to tell them – my two girls who are now 12 and 19. I even apologized to them for being so stressed out for that week two years ago.

Much to my surprise they both told me. “Dad we don’t remember you being stressed or not having a good time, we had fun and thought you did too”.

I get the goose bumps as I write this because in my mind I thought my behavior was different and they noticed. I guess I hid it well enough and when I took my calls on the deck they didn’t think anything of it – other than Dad’s just doing some needed business while on vacation.

Either that or they just wanted to make me feel good. Of course, when they asked about it (being the ever-pontificating Dad that I am), I turned the whole story into a little life lesson and shared with them some of the inner workings of what was going on in my business at that time.

I know they were listening…but they’ll never truly understand what I was going through that week until they go through the same kinds of things themselves…and come out the other end wiser and stronger.


The reason I share this with you is to let you know that especially if you are getting started in this businessyou will face your own challenges and you will face adversity.

How you deal with those challenges and that adversity is what will set you apart and make you successful or not. It’s far easier to write this long after I experienced it because it taught me a lot – but at the time, I’ll never forget how stressful and painful that week was.

But I got through it…and so can you when your time comes as well.

This vacation was so much more relaxing and amazingly stress free. But the funny thing is that my kids loved them both and probably didn’t notice any difference.

I sure did. And although the vacation two years ago for me personally was one I’ll never (but would love to) forget…it makes me appreciate the one I had this past week even more.

If you made it this far – please leave a comment below! If you are new I would love to hear what are some of your worst fears as a new investor? And if you’re  experienced please share your horror stories below…and what did you learn from them?

I am sure you veterans have more than a few stories to share – so please share them by leaving a comment below!

About Author

Mike LaCava

Michael LaCava is a full time real estate investor, house flipping coach and the President of Hold Em Realty located in Wareham, MA. He runs the website House Flipping School to teach new real estate investors how to flip houses and is the author of "How to Flip a House in 5 Simple Steps".


      • Jeff Brown

        Bought a 9 unit apartment building to rehab. All studios, pretty cool location, but transitioning to cool, if you know what I mean. I close escrow and THAT week get a call from a police sergeant. Will I cooperate with the police in cleaning out that building? What?!! Huh?!! I’d inspected everything to death, including all leases. Everyone I met, the tenants, were cool, though I hadn’t met them all. The owner had obtained the paperwork (estoppel agreements) from tenants who were gone during my THREE inspection visits.

        Anywho, back to the cops, I said that of course I would, what was the problem? To make a long story short, he didn’t take a breath for almost three minutes. Holy crap on a cracker. Turns out people from 25 miles away were gettin’ their drugs there. Also, while they were there, female companionship was available for a fee.

        It wasn’t SWAT but the action they took was identical. Seven cars, two vans, plus Vice was there, and to my surprise so was animal control. After meeting up a half mile away to ensure everyone was on the same page, they, with me in tow, headed to the property.

        The Vice guys (I swear they looked like Miami Vice.) knocked on the front door. When a guy I’d NEVER seen answered, they pulled him on to the front porch, slammin’ him to the floor. He was huge, but went down like a puppy. That’s when several cops, guns drawn, went through the front door. I learned later the same number had busted through the back door too. After a few minutes the parade of cuffed ‘tenants’ began exiting to the street and into the vans. Then out of nowhere rang two gunshots. Holy crap on a cracker. My mind immediately saw all money gone forever. Apparently one of the cops had inadvertently cornered a full grown male Doberman, who’d decided he wasn’t gonna surrender his ‘turf’. It took two shots to stop the poor animal.

        That was the day Dad laughed at dinner, hearing the story. He then mocked me, saying, “So, Son, are you now gonna listen to me and get the estoppel agreements from the tenants yourself, and in person?”

        Um, yeah. That was almost 30 years ago. I’d rather of learned the easy way. 🙂

        Epilogue: After completing roughly 10% of the rehab, one of the local potential buyers I’d contacted, a local group of Buddhists, returned my call. They bought it for cash to use for their monks. We made well over 20% on that deal, which proves that even a blind squirrel finds an occasional acorn every now and then. 🙂 Lucky doesn’t come close to describing it.

        • Thanks Jeff.
          Now thats going to be tough to beat.
          Lets see if anyone tries to beat that story.

          Should of listened to dad. Lol.

          Thanks for sharing

    • Hi Nicole-

      So true. I am just keeping it real. There is a lot of good in this business but everyone must realize in any business venture you will stumble and run into problems. It is how you react to them which makes the difference.

      Thanks for your comments

  1. Great article!
    Worst one for me was when I gave my partner carte blanche on a rehab. It was my money in the deal. He went over by double and we’ve had the house for 10 months! We’ve lowered the price multiple times-looking at a big loss.
    What did I learn? Lots-how to manage a rehab. Using draws, released upon certification of work completion. Getting multiple bids. Getting references. Etc, etc.
    Expensive tuition, but I learned the lesson!

    • You’re not alone Travis in this example. I have heard this one for sure a few times.
      The good thing is you learned from it and improved and put in systems not to repeat.
      Always improving no matter what level your business is at.
      Great job.

    • Hello Travis, I feel your pain, my contractor partner and I were on our 2nd and 3rd renovation (at the same time). As he was controlling one, I handled the other. I gave him control of the checkbook as it was “EASIER” for me as the two properties were about 50 minutes away from each other. As we got closer to ending one, I kept telling him that we only have this much in the budget can you finish it? His answer was of course that is enough money? Well 6 months later he finally finished the project at twice as much as we anticipated. Worse part about it was he was paying himself weekly as I didn’t see a dime. We finally have it under agreement and schedule to close on 8/26. First deal I have ever done where I am losing money on.

      Lesson learned like you said.

  2. Worst nightmare for me was I had just gotten back from a trip to Europe and the building inspector from the town I had a 6 unit had a message on my voicemail saying that he knew I was “harboring drug dealers in my lower unit” (which was vacant btw) and that the SWAT team was poised to “take us down” that night and seize the property. As I was listening in my bathrobe jet lagged form the flight that first AM back, I nearly fell over…instead I called my lawyer.

    When I came to, I spoke to him he said he didn’t care and that I was a “damned liar” for telling me that the guy who had used the address for the building I owned who up on multiple drug dealing charges and that it was too late and the SWAT team was “on their way” to storm the building.

    My property manager told me that the week before he had in fact sent a SWAT team to seize the building next to ours – and he want kidding. I talked him down and he rescinded the threat after we sent delivered all our leases to him to show him the unit was vacant.

    He “retired’ the next week as many other landlords had gotten similar kinds of calls. THAT was a hell of a vacation Ill never forget!

  3. Wow, what is WRONG with people?! Meaning the selectwoman who gave you such a hard time for purely petty personal reasons and tried to sabotage your reputation. It’s scary people like that are in power. I’m glad it worked out in the end for the family gaining title to the house and kudos to you for sticking to your word even though it cost you a painful amount of time and money. I’m happy your business overcame that difficult time and is doing so well.

    I am not on your scale at all, but I just don’t understand how people can hate RE investors so much when it’s clear as day that what the RE investors are doing benefit the neighborhood and community.

    I’m glad to hear your vacation this time around was much more pleasant for you!

    And @Jeff Brown and @Ralph, wow, those were some stories!

    • Thanks Michelle,

      It bothered me for a while and I took it personally. A friend of mine gave me a book called the 4 agreements and it is a short read. I read it 4 times as a reminder so I don’t fall back.
      The 4 agreements are
      1- Don’t take things personally
      2- Don’t make assumptions
      3- Be impeccable with my word
      4- Always do my best at everything

      Its not always easy but it really works and has helped me overcome some of those feelings.

        • Michael, that is some great advice. As long as you do what is right, at the end of the day, don’t worry about what other people say. If you go out there and do your best for the community a your business, you have nothing to hang your head.

          We are in the business of solving problems. You need to have thick skin and shake off what other people say. Remember, if people weren’t jealous of you, they would never say anything bad about you. They are just jealous because they don’t have what it takes to do what we do!

Leave A Reply

Pair a profile with your post!

Create a Free Account


Log In Here