Costly Asset Protection Mistakes Investors Keep Repeating

Costly Asset Protection Mistakes Investors Keep Repeating

Stuart UdisPro Member
Attorney · Philadelphia · Member since 2018 · 2k+ posts · 3k+ votes

Here are some of the costliest asset-protection mistakes I see investors make. Most mistakes start with misunderstanding how protection actually works, and many are reinforced by well-intentioned but inaccurate Bigger Pockets forum advice. Here are the recurring issues I see most often. These are not listed in any particular order. 

1. Waiting until a portfolio hits a certain size (often 10 units) before titling real estate into an LLC. Restructuring a portfolio later from retitling properties, updating insurance, revising leases, notifying lenders, and cleaning up years of past operations is far more expensive and disruptive than forming the correct entities upfront.

2. Creating extra entities to act as the manager to sign leases, collect rent, or communicate with tenants. If the manager entity has no real business purpose, it’s treated as an alter ego. It offers no meaningful protection and can actually cause complications with insurance coverage when issues do arise.

3. Failing to maintain and operate your entities correctly. This starts with following the operating/partnership agreement. 

4. Forming LLCs in states that are recognized for anonymity This does not prevent liability or lawsuits. The deed holder which is publicly listed in the local recorder of deeds is all anyone needs to identify the real estate owner and file a claim. 

5. Forming LLC's in states with favorable charging order protections. Understanding how real estate disputes are often resolved, means these protections are rarely relevant. Why fight the unnecessary fight as a defendant or creditor when there's real estate where a judgement/ lien can be attached clouding title until paid off?

6. Forming an LLC in Delaware to benefit from the "stronger case law" or business-friendly courts is rarely useful for real estate investors. If your business involves owning rentals or renovating and selling property, nearly every claim will be handled in the state where the property is located, not Delaware. In most situations, the Delaware courts will never be the proper venue.

7. Entity structures that restrict or limit which banks or lenders are willing to work with you. I am not referring to loan products that require real estate to be titled to your name such as FHA financing. I am referring to lenders who will lend to real estate titled to entities but won't finance your transactions because your entity structure is unnecessarily complexed or your organization documents look like they were prepared by a 3rd grader.

8. Carrying incorrect or insufficient insurance or operating your real estate business in a manner in which coverage will be excluded.

9. Buying umbrella insurance believing it's a cure-all without understanding when the coverage actually applies. Many assume umbrella policies cover any major loss or claim, but umbrellas coverage is surplus general liability coverage meaning the primary coverage must be exhausted and generally only applies to substantial personal injury claims if applicable. 

10. Hiring vendors or contractors who are uninsured or improperly insured. This is one of the fastest ways to inherit someone else’s liability. If a contractor isn’t carrying valid general liability and workers’ comp, any injury or damage can fall directly on the property owner. Often your own insurance coverage carries exclusions if hiring uninsured vendors or performing tasks that require permits. 

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Henry ClarkPro Member
Developer · Member since 2020 · 4k+ posts · 4k+ votes
10mo

OP I would expand on operation procedures and rental contracts.   Although they may not prevent liability issues, they will mitigate exposure.

1.  Snow ice removal

2.  Annual mitigation. Fire and carbon monoxide testing and battery replacement.

3.  Dryer and fireplace inspection cleaning

4.  Contract documentation regarding why you do and don’t accept tenants.

5.  Contractor vetting process as mentioned above.

6.  Tenant insurance requirements so it is clear cut about bug, water damage, offsite housing,  etc  

See this reply in the discussion

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  • Realtor · Oklahoma City · Member since 2020 · 258 posts · 139 votes
    10mo

    @Stuart Udis

    Great post & I concur that this is a very valid list that many people get held up on. 

    Consistently learning & improving one's personal portfolio, structure & operations can all greatly help reduce the risks many fear. 

  • Henry ClarkPro Member
    Developer · Member since 2020 · 4k+ posts · 4k+ votes
    10mo

    OP I would expand on operation procedures and rental contracts.   Although they may not prevent liability issues, they will mitigate exposure.

    1.  Snow ice removal

    2.  Annual mitigation. Fire and carbon monoxide testing and battery replacement.

    3.  Dryer and fireplace inspection cleaning

    4.  Contract documentation regarding why you do and don’t accept tenants.

    5.  Contractor vetting process as mentioned above.

    6.  Tenant insurance requirements so it is clear cut about bug, water damage, offsite housing,  etc  

  • Stuart UdisPro Member
    OP
    Attorney · Philadelphia · Member since 2018 · 2k+ posts · 3k+ votes
    10mo

    @Henry Clark You hit on some great add on points. I would categorize items 1-3 from your list as proactive asset protection measures. Snow and ice removal systems are essential to avoid premises liability claims. Meeting fire safety requirements is just as important, and one of the easiest ways a property owner can trigger an insurance exclusion by failing to comply with local requirements. Preventative maintenance like dryer vent cleaning and fireplace maintenance are some of the best ROI's by extending the life of major systems.

    Glad you mentioned contracts. Contract management is another area that is often overlooked. The process of preparing and negotiating contracts forces everyone to slow down and address timelines, scopes of work, insurance requirements, and the allocation of risk. That alone prevents many disputes that typically arise later.

    Expanding on tenant insurance, managing both vendor insurance and tenant insurance through leases and vendor contracts can shift risk. Additional insured requirements, when used properly, move primary insurance obligations away from the owner and onto the parties creating the exposure. This helps keep premiums low and reduces liability exposure. 

    Sadly, it is usually the new investors who spend $10K on complex asset protection structures but fail to take any of the practical steps you mentioned. Some even admit they no longer have the budget for basic operational safety because of what they spent upfront. This happens because many investors are taught to focus on preparing for liability events rather than preventing those events through sound operational practices.

    The result is that they invest heavily in legal structures while overlooking the day to day systems that actually reduce risk: maintenance, compliance, insurance management, and disciplined vendor oversight. Most cannot even articulate how or why the expensive structures will benefit them, because the emphasis was placed on fear and liability instead of understanding how good operations eliminate most of the exposure in the first place.

  • Investor · Milwaukee - Mequon, WI · Member since 2010 · 5k+ posts · 7k+ votes
    10mo

    I would add that a poorly set up (and operated) LLC for a new investor combines the disadvantages from not having one and having one in a nice package of just downside and no real benefit. Meaning you don't get any protection out of it while you have to deal with it, move the tile behind the back of the bank, because of a low interest rate residential loan - or you a higher rate commercial 5 year balloon - risky for its own reasons.

    You will probably disagree with me here, but personally I believe that if you start out and buy a 200k single family with 20% down the disadvantages of an LLC outweigh the potential benefits by far. If you buy 5+ units MF it's a different story.

    I was curios a while ago and asked if anyone had ever been actually protected by an LLC and while the post got a lot of responses, but nobody had a clear yes to the question. https://www.biggerpockets.com/forums/926/topics/1151922-than... 

    So to me it comes down to probability and risk tolerance. Personally I have never been afraid to go outside during a thunderstorm, but you can correctly argue that people have been struck and killed by lighting.

    • Don KonipolBusiness Member
      Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
      10mo
      Quote from @Marcus Auerbach:

      I would add that a poorly set up (and operated) LLC for a new investor combines the disadvantages from not having one and having one in a nice package of just downside and no real benefit. Meaning you don't get any protection out of it while you have to deal with it, move the tile behind the back of the bank, because of a low interest rate residential loan - or you a higher rate commercial 5 year balloon - risky for its own reasons.

      You will probably disagree with me here, but personally I believe that if you start out and buy a 200k single family with 20% down the disadvantages of an LLC outweigh the potential benefits by far. If you buy 5+ units MF it's a different story.

      I was curios a while ago and asked if anyone had ever been actually protected by an LLC and while the post got a lot of responses, but nobody had a clear yes to the question. https://www.biggerpockets.com/forums/926/topics/1151922-than... 

      So to me it comes down to probability and risk tolerance. Personally I have never been afraid to go outside during a thunderstorm, but you can correctly argue that people have been struck and killed by lighting.

      I’ve settled a couple of lawsuits cheaper than I would have been able to if all my assets were exposed rather than just the one specific to the series of the LLC.  I can’t “prove” I was able to settle cheaper, or that the plaintiff would have not settled for the amount they did; just as you can’t “prove” someone didn’t sue because your assets are “protected”, but the empirical evidence is clear.  

      If your chances of saving your a…. by simply having each property in a LLC rather than personally is small, say 1 out of 200.  For those who only own one asset in their life, that’s only a 1/2 of one percent chance.  But for those who are active in real estate; I’ve owned probably 300 properties; 400 notes, 15 businesses, and many more partial interests; the 4 or 5 times The outlier event occurred is well worth the cost of protection.  

      Attorneys are attracted to the most amount and the easiest assets; if those assets are off the table and much less assets exposed the plaintiff will have to (1) obtain services of a less successful attorney (2) fund the lawsuit himself rather than be able to on a contingency basis (3) have their attorney willing to put in “less effort” in pursuing the claim.  

      There are no hard and fast rules. Rather than random try’s at limiting liability (which may be better than nothing) anyone having, or anticipating having even relatively modest net worth should have an asset protection PLAN in place.  And this plan for those with assets up to say $10 million is going to be very STATE SPECIFIC based on their state of residency.  
      Private Mortgage Financing Partners, LLC
    • Investor · Milwaukee - Mequon, WI · Member since 2010 · 5k+ posts · 7k+ votes
      10mo
      Quote from @Don Konipol:
      Quote from @Marcus Auerbach:

      I would add that a poorly set up (and operated) LLC for a new investor combines the disadvantages from not having one and having one in a nice package of just downside and no real benefit. Meaning you don't get any protection out of it while you have to deal with it, move the tile behind the back of the bank, because of a low interest rate residential loan - or you a higher rate commercial 5 year balloon - risky for its own reasons.

      You will probably disagree with me here, but personally I believe that if you start out and buy a 200k single family with 20% down the disadvantages of an LLC outweigh the potential benefits by far. If you buy 5+ units MF it's a different story.

      I was curios a while ago and asked if anyone had ever been actually protected by an LLC and while the post got a lot of responses, but nobody had a clear yes to the question. https://www.biggerpockets.com/forums/926/topics/1151922-than... 

      So to me it comes down to probability and risk tolerance. Personally I have never been afraid to go outside during a thunderstorm, but you can correctly argue that people have been struck and killed by lighting.

      I’ve settled a couple of lawsuits cheaper than I would have been able to if all my assets were exposed rather than just the one specific to the series of the LLC.  I can’t “prove” I was able to settle cheaper, or that the plaintiff would have not settled for the amount they did; just as you can’t “prove” someone didn’t sue because your assets are “protected”, but the empirical evidence is clear.  

      If your chances of saving your a…. by simply having each property in a LLC rather than personally is small, say 1 out of 200.  For those who only own one asset in their life, that’s only a 1/2 of one percent chance.  But for those who are active in real estate; I’ve owned probably 300 properties; 400 notes, 15 businesses, and many more partial interests; the 4 or 5 times The outlier event occurred is well worth the cost of protection.  

      Attorneys are attracted to the most amount and the easiest assets; if those assets are off the table and much less assets exposed the plaintiff will have to (1) obtain services of a less successful attorney (2) fund the lawsuit himself rather than be able to on a contingency basis (3) have their attorney willing to put in “less effort” in pursuing the claim.  

      There are no hard and fast rules. Rather than random try’s at limiting liability (which may be better than nothing) anyone having, or anticipating having even relatively modest net worth should have an asset protection PLAN in place.  And this plan for those with assets up to say $10 million is going to be very STATE SPECIFIC based on their state of residency.  

      I can see the deterrence factor, especially when the plaintiff has money and can afford a good attorney. Jordan Peterson comes to mind: If you are showing your teeth, you may never have to bite. 

      You mention $10M, I think net worth is an effective filter. New investors don't have enough net worth to become a target, the juice is juist not worth the squeeze. I think that changes around that time when you run out of conventional loans and have to start using commercial lending. At the point the lender will require an entity. 10 properties would be roughly 500k in net worth, maybe a million, I can see how that starts looking interesting for an attorney. So there is a natural evolution. 

      In my mind the classic situation is tenant is sueing landlord, but does not have any money to pay attorney, so the attorney gets half of the damages and has to do now math of probability x payout = worth my time? 

      But I am not an attorney, what do you think Stuart?

  • Stuart UdisPro Member
    OP
    Attorney · Philadelphia · Member since 2018 · 2k+ posts · 3k+ votes
    10mo

    @Marcus Auerbach You are absolutely correct that very few investors actually operate their entities correctly. I also agree with your position on early acquisition financing to a certain extent. Perhaps not the 20% down conventional financed single family home because most community banks will match those terms for an LLC borrower as long as the guarantor is solid. A better example would be the ability to use more favorable loan products such as FHA financing. That can be an incredible accelerator and ROI lever, and it would be unwise for investors to ignore access to 97.5% leverage when they understand how to use the leverage responsibly.

    I do believe LLCs provide protection, but perhaps in a different way than your earlier forum post suggested. For one, using an LLC correctly reduces the likelihood that your personal name appears on a docket. That alone avoids the long-term nuisance of explaining prior claims. LLCs are also valuable business planning tools. Nobody knows what the future holds, and it is far easier to admit a new member into an existing LLC than it is to retitle real estate after the fact.

    An LLC can also limit liability exposure, although real estate is a unique asset class where the property itself reduces the motivation for most plaintiffs to pursue personal assets. It is far easier for a creditor to attach a judgment or lien to the real estate, cloud title, and get paid when the property sells or refinances. There is little incentive to spend additional money attempting to pierce the entity, outside of rare circumstances that simply do not apply to the overwhelming majority of real estate investors. This is of course when insurance is not relevant which it often is. This is why I cringe when I see the asset protection service providers use fear tactics to convince an investor in NJ to create an entity structure involving entities in NV or WY citing the better charging order protections knowing the fact pattern will rarely arise where that's even relevant.

  • Henry ClarkPro Member
    Developer · Member since 2020 · 4k+ posts · 4k+ votes
    10mo

    OP to expand on protection regarding an LLC.

    1.  Have it owned within a Trust.

    2. Make sure the LLC is the holder of the insurance. The insurance Lawyers will handle the litigation as long as you followed procedures and documented. Have them or your attorney review contracts and procedures.

    3.  LLC operating agreement.  Make sure it is recorded.  Have your attorney or your insurance company review your Operating Agreement.  Look at stopping distributions.  State of operations. 

    4.  LLC ownership liability exposure.  Have an attorney review your LLC operating agreement.  Make sure you have a built in, exit strategy.  You have a greater chance of having liability exposure through divorce or ownership dissolution than a customer, vendor or bypassed exposure.  

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