All Forum Posts by: Ryan Cleary

Here's the situation: (this is hypothetical)

-Bought a house and used it as a primary residence for over two years

-Rented the house out through airbnb in the summers while we were traveling

-Would love to take advantage of not paying capital gains taxes when selling the property (live in flip)

-Not sure how the STR income will affect that

My fiancee and I are planning on continuing our live-in flips. However, since we are both going to be working remotely, we were thinking about living in our next home from September to January, then traveling in a van for the remainder of the year. Instead of leaving the house vacant, we are purchasing in a fantastic STR market, so we will prepare it for rentals and list it through Airbnb, etc.

Now, I am not sure how this STR income will affect us when we sell the house (completing the live-in flip). I am aware that if you buy a duplex with a long-term rental, you are only able to complete half of a live-in flip, but short-term rentals... I don't know how it would be looked at.

I too would like to get into flipping in the near future but it would be coming from a position of strength (having a decent portfolio of long-term rentals)

Maybe starting out you can try a live-in flip!  My fiancee and I successfully completed a live-in flip and it put us in a fantastic position

Very impressive Nathan!  I know you have helped me out a bunch, the world needs more Nathans!

Does anyone have a manager in Columbus they would recommend?

Our sailing adventure is ending in a few months.  We plan on moving to a different (investor friendly) state and continue house hacking.  It’s almost as if we are starting life over with the benefit of having a decent portfolio and about 150k cash.

My fiancée and I plan on getting our realtor licenses but starting out I was going to find a W2 for security and ease of underwriting.

Thought it would be fun to ask the community what career paths they recommend for investors 

I'm currently taking a break from my New York realtor career to go on the adventure of a lifetime (sailing around the world with my fiancee) and we have determined for a long time that we are not going back to New York.  We have family and some rental properties in Palm Beach county.  So we were planning on getting licensed down here.  I was curious if anyone knew of any investor-friendly brokerages down there.  I would love to explore them!

 Thanks for the reply Marcus!  Seems like you and I would get along

Over the past 3 years, my girlfriend and I have acquired 4 rental properties.  We then quit our jobs, bought a 40' catamaran, and have been sailing around the world since this April of this year.  The only problem is that we are still in our 20s and still have the hunger to grow our portfolio.  We don't depend on our rental income to live.  We have a small amount of money saved that we keep separate for our sailing adventure and we will stop sailing when that runs out.

We have one property where we can potentially cash-out around $55,000 using a non-qm product, however this will reduce the cash-flow of this property(not that big of a deal).  We would love to purchase another property but are just concerned with the possibility to make it happen (regarding underwriting) without having income.  

I would love to see if anyone has some creativity in this situation.  Thanks!