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All Forum Posts by: Dan Cahill

Dan Cahill has started 10 posts and replied 47 times.

Post: Seller fi potential deal

Dan CahillPosted
  • Posts 47
  • Votes 7

Looking into this possible deal: https://drive.google.com/file/...


seems a bit overpriced, but great location.  Seller fi potential has me intrigued, possibly some creative financing opportunity.  
curious on anyone’s thoughts, thanks!

Quote from @Bill B.:

Very true. Self directed roths with enough to invest in RE instead of stocks is rare. Good job. 


 Thanks!

Quote from @Bill B.:

I wouldn't buy any real estate in a retirement account. Real estate is already a tax advantaged investment. BUT, if you insist. You don't want appreciation (something that should be taxed at 15%) to be taxed as regular income. (Which it would if it was in an IRA, resulting in a 50-100% increase in taxes.)


Ahh, but it's a Roth IRA. My understanding is the ordinary income tax on self-directed IRA's only applies to traditional IRAs.

Quote from @Bill B.:

Yes. Preferably something that’s supposed to bring in income, not appreciate. You don’t want to turn 15% capital gains tax in to max tax rate income. Save appreciation for your regular non-ira funds. The funds you should never have to pay any taxes on. (Exchange and hold and hold and exchange until you die…)


Not 100% sure I follow. are you saying OK to buy a high income generating, low appreciating property with the use of combined Roth IRA/non-IRA funds? and then what about exiting in the future - wouldn't it just be capital gains tax upon sale (or none if I 1031)?

Quote from @Dmitriy Fomichenko:

@Dan Cahill

While it is technically possible in some circumstances to structure such a transaction, in most cases it would be considered "prohibited transaction" in the eyes of IRS, or likely to lead to a prohibited transaction in the future. All transactions involving your IRA must be "arms length" so if you want to sleep at night make sure that you nor any other "disqualified person" is involved in the transition with your IRA. 


Agree on probly being more trouble and risk than it's worth. I think if I make any RE investment with IRA funds it will be as an LP instead of direct RE

Quote from @Greg Scott:

Boom - Sound of an IRA blowing up.

The IRS doesn't want you to be able to create a situation where you could shift taxable dollars to non-taxable dollars.


 the logic makes sense..even if no definitive code section or reg. addresses this scenario, I see the elevated risk level.  Thanks

I know an IRA can be used to purchase real estate, but can I combine IRA funds with non-IRA funds to buy a single property? I.e. I would see it as a partnership from a tax perspective, with IRA owning a portion, and myself owning the rest. Would be for an investment property, not personal use.

Post: Buying investment condo

Dan CahillPosted
  • Posts 47
  • Votes 7

Thanks, Sean.  I'm of a similar mindset - go where the great opportunities exist, wherever those may be.  If a certain asset class is compelling enough within my local market, I'm all ears.  

Post: Buying investment condo

Dan CahillPosted
  • Posts 47
  • Votes 7

I appreciate all the thoughtful replies.  After thinking about it, I have decided for now to not go down this path; primary reason being the time and effort involved with acquiring/managing a portfolio of condos just isn't what I desire.  

I'm continuing to look in the commercial space in the Boston area, around $1Mish or less, but haven't found any compelling deals to date.  

Post: Buying investment condo

Dan CahillPosted
  • Posts 47
  • Votes 7

Is now a good time to buy condo's in Boston suburbs?

My mentor/broker is now advising I consider building a portfolio of condos, instead of CRE

It's still a hot housing market here, so one must act quickly when a listing pops up

Meanwhile cash earning 4.4% risk free in MM fund.  

This would be my first foray into real estate investing (I do own my own home as well).  I like this particular suburb (Natick), but am always fearful of buying assets when things are hot/bubbly.  I can generate income through MM fund/treasuries/dividend stocks/selling covered calls/cash secured puts, without ever leaving my home or having to deal with tenants.  I'm not adverse to putting in a little work owning RE, it's just I feel recession risk is very real right now, and there could be some great deals to be had in the not too distant future.  Any advice is appreciated.