Gather Circle

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Gather Advisory

Onboarding Questionnaire

Welcome to the Circle. This questionnaire is how we get to know your numbers, your goals, and the kind of property that actually fits your life. Your answers shape your buy box and the deals we bring you, so the more honest and specific you are, the sharper we can be from day one. If you’re not sure about any answer, give us your best estimate and we’ll refine the details together on your call.

8 sections

About 15–20 minutes

Section 01 of 08

The basics

First name *

Last name *

Best phone number *

Best email *

What state do you live in? *

What’s your best means of communication? *

Choose all that apply.

Text

Scheduled meetings

Phone calls

Do you own your primary residence? *

Yes

Do you currently own any short-term rentals? *

Do you own any other type of real estate? *

Section 02 of 08

Your income and tax picture

This is the foundation of your tax strategy, so real numbers matter here.

What’s your filing status? *

Single

Married filing jointly

Married filing separately

Head of household

Approximate household W-2 income for this year *

Your best estimate for this year.

If married, does your spouse also work a W-2 job? *

Yes

Partially

Spouse’s approximate income (Optional)

If applicable.

Best estimate of your marginal (top) tax rate — federal and state combined *

If you’re not sure, give your best guess and we’ll refine it together.

Do you currently work with a CPA? *

Yes

If yes, do they understand the short-term rental tax strategy and cost segregation? (Optional)

Yes

Not sure

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Section 03 of 08

Tax strategy viability

The short-term rental tax benefit only works when the person claiming it both owns the property and puts in the hands-on hours to run it. These questions confirm the strategy fits your setup before we build around it.

Who will own the property with you? *

How will ownership be split? (Optional)

Only if you have a co-owner.

Your ownership (%)

Co-owner’s ownership (%)

Who will be the primary owner claiming the tax benefit? *

Me and my spouse jointly

Split with my business partner

Not sure yet

Who will materially participate in setting up and running the property in year one? *

Materially participate = personally doing the hands-on work of running the property.

Just me

Me and my spouse

Me and my business partner

My business partner

Combination

Do you plan to use the property yourself? *

Heavy personal use can change how the property is taxed, so it helps to know your plans up front.

No, this is purely an investment

Occasionally — two weeks a year or less

Yes, regularly (more than two weeks a year)

Not sure yet

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Section 04 of 08

Capital and financing

How much capital do you have available to deploy into your first property? *

A dollar figure.

Where does that capital currently sit? *

Of that, how much toward (1) down payment and closing costs, and (2) design, furnishing, and amenities? *

How do you plan to finance the purchase? *

Choose all that apply.

Conventional loan

Second home loan

DSCR loan

All cash

Open to creative financing

Need your guidance

Are you pre-approved or already working with a lender? *

Yes, pre-approved

Working with a lender, not yet approved

I’d like to work with a lender you recommend

No, not yet

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Section 05 of 08

Your priorities

Every deal balances three things — Flow, Grow, and Keep. Knowing what matters most to you tells us what to optimize for when we underwrite.

Rank these in the order that matters most to you

1 = matters most. Flow: monthly cash flow · Grow: long-term appreciation and equity · Keep: tax savings against your W-2 income.

Flow — monthly cash flow in your pocket

Grow — long-term appreciation and equity

Keep — tax savings against your W-2 income

In a sentence or two, what’s the main reason you’re buying a short-term rental right now? *

Do you have a target for annual cash flow? *

Do you have a target for annual property appreciation? *

Roughly how much of your income are you hoping to shelter from taxes this year? *

Do you have a target for first-year cash-on-cash return? *

Cash on cash = cash flow / total investment.

Do you have a target for first-year return on investment? *

ROI = (cash flow + tax savings + appreciation) / total investment.

How do you plan to manage the property? *

Self-manage

Co-host or hybrid

Full-service property manager

Not sure, advise me

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Section 06 of 08

Your target market

Where you invest shapes the returns and the kind of guest you’ll attract. We start with the market, then get specific on the property.

Do you have one or more markets in mind? If so, which ones? *

How far from home are you open to investing? *

Within a 2 to 3 hour drive

Within my home state

Within adjacent or neighboring states

Anywhere the numbers work

What type of destination appeals to you? *

Choose all that apply.

Mountains

Lake

Beach

National park adjacent

Wine country

City

Desert

Ski town

College town

Theme park or attraction area

Small town or countryside

Open to recommendations

How do you feel about seasonal markets? *

I want steady, year-round demand

A moderate peak season is fine, with income spread across most of the year

I’m comfortable with a strong peak, even if most income comes in a few months

No preference, show me the numbers

Are there any states or markets you do not want to invest in? (Optional)

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Section 07 of 08

Your buy box

Your buy box is the filter we underwrite against. The clearer you are here, the faster we can bring you the right deals. Open to recommendations is always a fair answer.

What type of property are you drawn to? *

Choose all that apply.

Single-family home

Cabin

A-frame

Townhouse

Condo or apartment

Multi-unit (duplex, triplex, etc.)

Tiny home

Barndominium

Unique or design-forward stay

Luxury villa or estate

Open to recommendations

How many bedrooms are you targeting? (Optional)

Leave blank if you’re open to recommendations.

Minimum

Maximum

How many bathrooms are you targeting? (Optional)

Minimum

Maximum

Do you have a target purchase price range? *

Minimum price

Maximum price

Who do you picture as your ideal guests? *

Choose all that apply.

Couples

Families with young kids

Families with teens

Large groups (reunions, celebrations)

Friend getaways

Business or remote workers

Pet owners

Open to recommendations

Are there any Airbnb or VRBO listings you find interesting? (Optional)

Is there anything you definitely do not want in a property? (Optional)

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Section 08 of 08

The bigger picture

Almost done. These last few help us understand what you’re really after, so your onboarding call starts on the same page.

What would make the next 12 months a success for you? *

Is this one property, or the first step toward a larger portfolio? *

What’s your biggest concern or hesitation going into this? *

Anything else you want us to know before your onboarding call? (Optional)

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