All Forum Posts by: Josh Surver

@Carolyn Fuller

So as long as I pay by credit card, debit card, or PayPal, etc… I don’t have to worry about the W2 and 1099? That would make things easy.

@Carolyn Fuller

So as long as I pay by credit card, debit card, or PayPal, etc… I don’t have to worry about the W2 and 1099? That would make things easy.

How do the tax ramifications of a hiring people to do small jobs (but over $600/year) work? I’ve heard you’re supposed to file a 1099 with the IRS and provide a copy to the contractor if you’re the one paying for the work, but when is the best time to do that and how do I got about issuing it?

If a contractor’s work spreads across the two years, do I file the 1099 for the year of job completion? Do I need to file a separate 1099 for each year if a partial payment was made in the first year prior to project completion in the second year?

@Matt Lane

I know some booking platforms like VRBO and PMSs (Guesty) use Stripe. I’m assuming it would work for long term tenants too.

@David Gauger

There's always the old fashioned method of checking what's available on the booking platforms in the market yourself! My friend has a STR on the east coast and he just manually checks what the other properties in the area that offer similar amenities are asking and prices just below them because he has few reviews than most in his area. He's crushing it. May be a good place to start for analyzing as a third method of comparison and pick an estimate in the middle of all the methods.

@James York

Congrats!

@Wilson Hunter

AirBnB hooks up newbie hosts like myself with SuperHosts who provide free suggestions. My guy told me no more than 30-35 photos.

@Christopher Dru

Hey! I have 3 thoughts for you:

You probably don’t need 10% of the property value in reserves - 6 months of expenses on both units would do. There’s an opportunity cost to your money. Put it into stocks or another real estate deal. If you don’t like that because stocks are getting crushed, doesn’t that mean it’s the perfect time to buy?

Another thought - since it’s a primary residence purchase, why don’t you put less down and use the cash to turn the unit you’re not living in into a short- or mid-term rental to boost the cashflow.

Third thought - cashflow looks low now, but how does it look 5 years from now after years of likely high inflation affecting rent and asset appreciation? Today’s returns are only a snapshot.

Investment Info:

Townhouse buy & hold investment.

Purchase price: $355,000
Cash invested: $60,000

First deal: MTR in CO Springs.

What made you interested in investing in this type of deal?

High leverage, high appreciation, & high cashflow.

How did you find this deal and how did you negotiate it?

Leah Keeling at Envision Advisors was my realtor and helped me find it on the MLS.

How did you finance this deal?

Secondary home loan at 10% down conventional financing.

How did you add value to the deal?

Turned it into a MTR.

What was the outcome?

Successfully cashflowing MTR in a high-appreciation area in my portfolio.

Lessons learned? Challenges?

Get good people on the team and anything is possible. Don't try to DIY furnishing from a distance.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Leah Keeling at Envision Advisors (agent), Paul Abaire at Armed Forces Bank (lender), Craig Kallian at Hoste (PM), and Bridgette Allen at AtYourServiceCOS (furnishing).

@David Gotsill thank you! I’ll reach out.