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All Forum Posts by: David Cherkowsky

David Cherkowsky has started 12 posts and replied 60 times.

I was asking myself the same question about a year ago while renting in nova. Ended up house hacking and have been very happy with that decision. Feel free to DM me. I'd be happy to provide details.

Post: House Hacking, Airbnb, first time home buyer

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25

Hi Bridgette, I actually just purchased a home recently and am implementing a similar strategy, living in the english basement and AirBnBing the upstairs. Some lessons learned from my experience:


- If there is a kitchen in the second unit, you can likely use the potential income generated from this unit to qualify for a mortgage. That obviously won't help the affordability, but will help qualify by raising your income in the DTI calculation. I recommend discussing this with your lender.

- Account for furniture costs - we furnished a whole ~2000 sqft house, but the costs were not insignificant. It ended up being ~$10k.

- Work with an agent that has experience with both house hacking and STRs. With AirDna pro, you can find comparable STR units and get a pretty strong idea of ADR and occupancy rates. This is invaluable when analyzing deals and something my agent helped with.

Are you calculating cash flow, ROI, etc. when opportunities pop up? I'd highly recommend doing that to ensure that you are making a smart financial decision.

Post: Starting my REI Journey in the Washington D.C. Area

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25

Hi Billy, house hacking in the area is a great way to get started. I'm maybe a few years ahead of you in my investment journey and would be happy to describe what's worked for me. Feel free to send me a DM.

Post: How can I be certain I can refinance ?

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25

How will you be financing it when you initially purchase it?

Post: New Investor Looking to Learn & Connect!

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25

@Jamal Kamara I think there's better folks in BP that can be speak to different areas of DC better than I could. I'm closing on a duplex at the end of this month and will be househacking in the Bloomingdale neighborhood of DC. I could provide better insight in a few months after getting some experience, but happy to answer any questions.

I think rent by the room is a good strategy in Alexandria because it allows you to house hack.  The main benefit there is house hacking allows you to put down a lower down payment than an investment property. You'll have to live in the property for a year before turning it into a full time rental, but you can rent it portions of the house the first year as long as you live there. Lots of good info on househacking on BP.

A traditional rental in this area probably won't cash flow at today's interest rates, and will require 20% down. I have one that I bought last year, and knowing what I know now, I may not have bought it.

Another strategy to consider close to Old Town is short term rentals. I think that's a way to get potentially positive cash flow in an appreciation market like northern Virginia. Only thing to be cognizant of is that laws vary by city. Alexandria city is the least restrictive area in the DMV for it, but if you're looking for something more active, a house hack with STR seems like the best option in the area to me. That's what I'll be doing in DC.

Post: New Investor Looking to Learn & Connect!

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25

Hi Jamal, from what I've seen, duplexes are pretty hard to find in northern Virginia, but DC has a lot. Have you considered expanding your search to across the river?

The best strategy for househacking in Alexandria seems to be a rent by the room strategy. Not that I have too much experience, but happy to chat more.

Post: How to Calculate DTI with Schedule E

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25
Quote from @Jay Hurst:
Quote from @David Cherkowsky:

Hi All,

I purchased an investment property in the middle of last year and to this point have been using 0.75*lease value in my DTI calculation. I have just received a draft of my tax return with the schedule E. I'm wondering how rental income is now calculated. I have heard the value from the schedule E is used (rather than 75% of lease). Can someone explain how the calculation works?

Thank you.

 @David Cherkowsky    This form is used:  https://content.enactmi.com/documents/calculators/Form1038.C...    This is what I recreated for you the other day. 


 Thank you Jay. This is exactly what I was looking for. Appreciate it!

Post: How to Calculate DTI with Schedule E

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25

Hi All,

I purchased an investment property in the middle of last year and to this point have been using 0.75*lease value in my DTI calculation. I have just received a draft of my tax return with the schedule E. I'm wondering how rental income is now calculated. I have heard the value from the schedule E is used (rather than 75% of lease). Can someone explain how the calculation works?

Thank you.

Post: Creative Financing for Airbnb in Northern Virginia

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25
Quote from @Jay Hurst:
Quote from @David Cherkowsky:

Hi all, I'm interested in thoughts on creative financing options for an Airbnb in Northern Virginia. A property is available off market that seems to be a great deal. I am interested in living in the basement, and renting out the upper unit on Airbnb. The property is likely a little too expensive for me to qualify for with a conventional loan based on DTI. However, I'm wondering if anyone has thoughts on creative financing. Maybe a DSCR loan? Any thoughts would be appreciated.

 @David Cherkowsky The above is absolutely correct, BUT do not assume you cannot qualify for a conventional loan. Make sure a competent LO with a NMLS number runs the numbers from you. My team has conversations all the time with borrowers, especially those that own real estate, that thing DSCR options are their ONLY options. But, guess what they are not loan officers or underwriters so they turn out to be wrong. (do not trust me to build the house, but I do know how to qualify you FOR the house.) Don't disqualify yourself without talking to an expert.


 Thanks for the response Jay. Just sent you a message.

Post: Creative Financing for Airbnb in Northern Virginia

David CherkowskyPosted
  • Investor
  • Alexandria, VA
  • Posts 60
  • Votes 25
Quote from @Sasha Mohammed:

Hi David,

There are lenders that will allow you to purchase via a DSCR loan using STR income to qualify. However, they will not allow you to live in the property at all, full stop.

This is because DSCR loans do not follow/ pass consumer protection laws. when you live in the property, it creates massive problems for this loan type and the lender which would issue it to you.

For that reason, most of these lenders want to ensure you OWN your primary residence. Some will let you rent your primary and still do a DSCR loan on the subject, however, this would come with the added scrutiny of really documenting and evidencing you have no intention of moving in to the subject.


Thanks Sasha. So I guess one option could be to do a DSCR loan, Airbnb the property in full, and then in the future, refinance into a conventional when my DTI allows me to down the road. For the property I'm considering, I think another year or so would allow me to qualify for a conventional.