All Forum Posts by: Yonathan Cabrera

 Understood! Thanks for the insightful response. And yes, connecting the dots served you well, I am NG, so my first ETS date is in 3 yrs. 

But just to clarify, you had an STR already before purchasing the $2M beachfront property? If so, where? 

My real intention on using STR's is really just because of the tax advantages that can be carried over to my active/earned income when I am finally settled down at an Airline in the future (currently in civilian flight school).

Do you believe I am overthinking using the Tax Code Section 469; "Real Estate Professional Status," and achieving that status with STR's or should I just stick with the proven LTR "House Hacking" strategy and build my RE Portfolio that way?

 Yes. The goal is to potentially begin a family once I have established basic seniority at an airline. I’m predicting that to be around 2030-31. 
That gives me between 2026-2030 to to build a foundation of 4 properties using the loan before I’m “settled down.” 

But when I am at this stage, do you believe regular conventional loans will be my alternative option to still scale up to, say, 10 properties without having to, "bounce all around the place," using the VA home loan.

 Hello Megan! I appreciate the encouragement on this! I concur 100% that it is an underutilized resource with it numerous benefits compared to, “civilian, conventional loans.” 

In regards to sharing your experiences and resources, would you mind if we connected and stayed in touch as I still have approx. 3 yrs before I’m even eligible to leverage it and just collect as much info as possible? 

Thanks! 

@John Underwood

Insightful, thanks! 
But when it comes to conducting Cost-Segregation studies to “accelerate” the depreciation of a property, can I still “carry over” additional entitlement from, for example, my first tax-year into the following years even if I am not meeting the REPS criteria through STR's?

@John Underwood

Understood, but do you think it should ever cross my mind in the future to dive into the STR realm so I can maximize tax-write offs (Passive losses offsetting active/earned income) from my Job later or just stick with the good, stable, LTR's?

@John Underwood

Thank you so much for reaching out on this for me! 
So, you are simply suggesting get my, "hands dirty," with Long term rentals, rinsing and repeating the "house hacking" strategy before even considering STR's and meeting REPS and Material Participation requirements to maximize tax write-offs on my future W-2, correct?

@Michael Baum

I greatly appreciate your insight on this matter. Just to clarify, I won't be eligible for my VA Home Loan until I am 23 (3 years more).

But what you’re encouraging is that when I am 23, I should use the first 4 or so years just building a portfolio of LTR’s and then when I am 27, look into leveraging STR's to meet the "Real Estate Professional Status" and "Material Participation" the IRS outlines, correct?

I am currently a 19 year old looking to simply gain as much financial education, simultaneously saving money for future investments. 

My biggest one would be leveraging my VA home loan in about 3 years. I want to know if it is possible to use this home loan for STR's since I know STR's (Under Tax Code Section 469) is one of the routes any RE investor can take to reach "Real Estate Professional Status," and so use passive losses from my property to offset active, earned income (My W-2 Job in the future).

Basically, does anyone know if this has ever been done? Using a VA home loan for STR conversion?

Thank You. 

And when you state, “to be boots on ground,” does that signify that I go to speak directly to eithe Vacasa or Evolve and ask to be, “boots on ground,” on their behalf to gain experience? 

And for FB groups, how do you suppose I write out my “post?” Should it br just a sincere, “I am an aspiring Co-Host and want to work as an intern for free to get job experience.” Or another approach?

Negative, if you could refer me to one it could be greatly appreciated