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All Forum Posts by: Matt W.

Matt W. has started 37 posts and replied 153 times.

Post: Are 1031's worth it on SFHs?

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83
Quote from @John Warren:

@Matt W. why not just sell one of your houses and test your theory? This way you get a chance to feel what it is like investing passively, and you still have a lot of the gains you can leverage if you want to pivot back into active investing. 

I would not sell and pay the taxes if you have 50 years to go..... that is a long time. I think you can continue scaling up and maybe focus on getting rid of certain parts of the responsibility? Why not hire a PM to help you take away some of the day to day frustrations if that is what is bogging you down? 


 Hi John, that's exactly what I'm doing at the moment. Set to close in a few days. I should net enough to do a minimum investment on two syndications after reserving money for taxes. I figure that 4 houses and (1/35th) of a self storage unit is more diversified than 5 houses. 

Post: Delaware Statutory Trust vs. 506B Syndication

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83

@Brian Burke

Thank you! I read the passage and it describes my situation perfectly. I think I'm too young and my numbers are too small to justify using a DST. Although I'll take a tax hit, I think on a 5-10 year timeline it will make more sense to invest in a syndication.

Post: Delaware Statutory Trust vs. 506B Syndication

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83
Quote from @Brian Burke:

I think what you are asking is whether a DST is better than an LLC. 506(b) just refers to the exemption from registration of your securities for public sale. Even a DST can utilize the 506(b) exemption.

So if my interpretation of your question is correct, it's hard to say that one is "better" than the other because they each have a use case.  

Most syndicates use an LLC structure because it allows flexibility in how you structure the offering. Most importantly you can get carried interest which in the simplest terms means that you, as the investment sponsor, can receive a percentage of the profits disproportionate to your capital contribution (even if you contribute no capital at all). You also have ultimate flexibility in how you execute the business plan. You can refinance whenever you want, you can do a value-add or heavy rehab, heck you can completely reconstruct the property if that's what is needed. But, most importantly, you can receive a share of the net profits from cash flow and appreciation.

The downside to the LLC structure is that you cannot accept 1031 funds into the LLC because units of an LLC are not like-kind property to real estate.

To solve the problem of accepting 1031 investors, sponsors started accepting money from their investors and putting them on the deed as fractional fee title owners. This was called a TIC structure because each owner was a Tenant In Common on the deed. This created all sorts of problems, mostly because there was no centralized control over the asset, and also because there was a lack of alignment of interest on the part of the sponsors--and even some corruption--so the TIC industry earned itself a very bad reputation after the market collapse a decade or so ago.

The DST concept was a response to the downsides of the TIC structure. It solved the issue of decentralized control by holding the property in a trust (the Delaware Statutory Trust, specifically) and the investment sponsor (or an affiliate) was the trustee of the trust. So now you have a structure where, similar to the LLC concept, the sponsor has control of the asset and the investors own beneficial interests in the trust, just like investors own units in an LLC. But the upside is the IRS ruled that beneficial interests in a DST were like-kind to real estate and thus qualify as replacement property in an exchange.

But just like everything else in real estate, there is no perfect solution to solve every problem and the DST is no exception--it comes with its own limitations and downsides. The primary limitations are what is called "the seven deadly sins". I'll just focus on the ones most important to you as a sponsor.

First, you cannot raise any additional capital.  Now if you raise enough in the beginning (which you always should anyways), you should be fine.  But you need to be aware of it.  Once the offering is filled, that's it.  No capital calls, no new investors.

Second, you cannot refinance the property and take out cash.  Nor can you renegotiate the terms of any existing loans. 

Third, and I think this is one of the most limiting factors--you are limited to making capital expenditures only to the extent as required for normal repair and maintenance and minor non-structural capital improvements.  So this means no heavy value-add projects and major rehabs.  

Finally, the DST structure is complex and this is not the same as an LLC syndication. You have to create multiple entities, one to be the trustee, one to be the master lease tenant and in some structures other entities as well.

And...in a DST you can't receive a promoted interest. In other words, you can't get a share of the profits in the same way as you do in an LLC structure. Instead, this is primarily a fee-based venture where you earn an acquisition fee, asset management, property management, and other fees. You can get some of the rental income via the way you structure the master lease, but you don't get a split of the property's appreciation.

So to sum it all up, it's not a matter of which is better. First you must ask yourself the question of what is the problem you are trying to solve? If it is that you have a lot of investors that want to invest in a value-add multifamily deal, LLC is your answer. But if you have a bunch of 1031 investors looking to trade into something, DST is the answer. You just have to be aware that from the lens of the sponsor these are two very different businesses.


Hi, I just found this thread 5 years later. (Currently reading "Hands Off Investor"). I'm coming at it from an LP perspective. I want to sell off my SFH rentals and get into passive investing. I originally planned to just sell my rentals, pay the taxes, and invest in various syndications. Now I'm hearing about 1031 DST's and how they might be better for me. I've talked to a couple DST "brokers" who were not that helpful, or possibly my understanding is just so low I can't grasp the difference of DST vs. Syndication. Any advice is appreciated.

Post: Are 1031's worth it on SFHs?

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83

Background; I've 1031'd 4 homes in the past 3 years. I either turned one home into 2 or traded a smaller home for a nicer home that will hopefully appreciate and cash flow more. 

My long term goal has always been to do the Rich Dad Poor Dad idea of "converting 4 red houses into one green hotel" and trading all my single family homes into various big commercial syndications. However, now I'm realizing that most syndications require a $500k-1Million investment if you want to use money from a 1031. Even if I had that much equity, it would be near impossible to sell them all within the timeframe. 

I get the benefit of the whole "swap til you drop" theory, but I (hopefully) have 50 more years to live and don't want to be carrying these houses forever. Now that I'm considering selling and moving the money into syndications, I'm confronted with just biting the bullet and paying the tax and the deferred taxes. It seems like the deferred taxes are just a monkey on your back that I'll have to pay eventually. Given, $100 today is worth more than $100 in the future due to inflation and the time value of money, but I'm not sure it was all worth it.   Thanks for any constructive feedback. 

Post: Lending for Repairs

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83
Quote from @Monica McCaskill:

I just inherited a property in Wilmington, NC which I would like to use as an investment property. The property does not have a mortgage. I need to make repairs to the home prior to renting it out (~$15,000). I am looking for lending options I can use to make all the repairs. I would like to use an option with lower interest than the credit cards I have used up to this point, and that I can pay off quickly using the rental income. Thanks! 

Hi Monica, message me if you'd consider selling!

Post: Taxes After Multiple 1031 Exchanges

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83
Quote from @Dave Foster:

@Megan Elliott, There's no statutory holding period.  But think of it as a spectrum of being able to demonstrate your intent to hold for investment use.  If you move into it day one that would be hard to demonstrate your intent to hold for investment.  At the other end of the spectrum the IRS gives you a safe harbor in Rev Proc 1008-16 at two years.  So, the answer is somewhere in between.  Most folks lean towards anything more than a year.  But it really is all about your intent and your individual fact set.


 So if you have 1031'd several times and have several million in equity/tax savings, can you move into a multi-million dollar beach house and clear it all? or is it only the $500k if married primary house rule?

Post: Newbie redeveloper DD

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83

Hey everybody, I'm looking for advice about redevelopment play. It involves two adjacent lots on a busy road right near my neighborhood. Both lots have small, run down houses on them, and I believe at least one has renters. I saw a handmade "for rent" sign and called the owner. I spoke to a woman who helps her older father manage the properties, and she says he wants to get out of the game.My question is how to structure the contract so as to give me plenty of time to make sure I can redevelop it in a way that makes sense? I already have spoken with a very experienced redevelopment specialist, and a big local builder/investor that have been very helpful, but they will only work with me so much until I have a property under contract.  I also don't want to waste their time on hypothetical deals. 

 My thinking is, assuming there is a tenant lease that must be honored, say at least 6 months, that should be plenty of due diligence time to hire the development specialist and make sure the project makes sense. I think I should give minimal or no due diligence/earnest money so I can walk away if it doesn't look worth it. Any advice is appreciated!

Post: Newbie from Webster, Texas

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83

Hey guys, super old post but figured I'd ask about Webster.  I'm considering an apartment deal out there and wanted your opinion about the town.

Post: Amazon Facility in Wilmington, NC

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83

@Alicia Marks

Don't let him live or buy at Campus Edge condos on Racine, it's all junkies and is hella sketchy. 

Post: Wilmington Investor Meet Up

Matt W.Posted
  • Rental Property Investor
  • Posts 157
  • Votes 83
Quote from @Alicia Marks:

I may be networking with you all soon. My son is looking at UNC Wilmington and I'll need a team to acquire a househack for him.


 Hi Alicia, 

I'm about to close on a house 1 block from campus, reach out if you want more info!