All Forum Posts by: Joshua Young

@Stephanie P. has a great point. Often times the legality of STR is overlooked, some municipalities are more open to them than others, some even put laws in place to promote vacation rentals. Of course these things can change at any moment so it's important to really do your due diligence and have a backup plan.

I had a roof pressure cleaning service back in college and buying a surface cleaner saved tons of time. I think you can rent them separately even.

Surface Cleaner

I've been hosting on Airbnb for a while (+5 years) and the location category is definitely the one I get hurt on the most. I think it's partly because people don't understand how to grade the location and Airbnb doesn't do anyone favors in this regard. In order to make "location" less ambiguous, I've seen hosts try to explain what it means in their listing descriptions. Not sure how well it works however.

Having one with the ability to use hot water will also make a difference but it's more of an investment. I guess it depends on how often you'll use it.

@Kerry Baird brings up a great point about the tax implications regarding flipping vs holding. I think as others are saying, holding is the best option for you and your comfort level.

I agree with @Timothy Church. Being booked out too far in advance is actually a bad sign in my experience and means you may need to adjust your prices upwards. After doing Airbnb for the last 5 years I can assure you, at least in my area (NYC), that guests are booking last minute more often and I'd expect that trend to increase.

I echo @Joe Sadusky!

I got primarily got involved in RE because I was motivated to find something beyond number crunching in a cubical. I worked as an analyst for REIT and was already doing the modeling for deals so I thought "why not do this for myself" and here I am.

Also, one thing I recently realized after starting a few non-real estate related companies, I like real estate because every property is different and requires a different perspective. It takes creativity, much like running a startup.

Thats really cool. Way to be creative and open to opportunities. Great work!

@Natalie Lalonde

That's pretty awesome! Did you know initially that you were going to rent it out as an SFR or did you figure that out later down the line? Just curious about the process.

North Carolina is the first place that came to mind when I read your post. As the title points out though you want to find a positive cash flowing property so it depends. Any of those states you mentioned have deals but you may need to be open to living in smaller metropolitan areas where markets are not as hot.