Quiz: Should I Sell My Long-Term Rental Property?

Quiz: Should I Sell My Long-Term Rental Property?

Instructions: Answer each question honestly. Tally your points at the end.

Scoring:

  • A = 1 point
  • B = 2 points
  • C = 3 points
  • D = 4 points

1. How well is your current tenant situation working out?
A) Excellent – long-term, reliable tenants
B) Mostly fine, but I’ve had some turnover
C) It’s been rocky
D) I’ve had frequent issues or vacancies

2. Is your rental property generating a healthy monthly profit (after expenses)?
A) Yes, consistently
B) Some months
C) Not really
D) It’s losing money

3. How involved are you in managing the property?
A) Not at all – my manager handles it
B) Occasionally involved
C) Too involved for my liking
D) I’m burnt out

4. Have you recently had to pay for major repairs or replacements?
A) No
B) Just one or two
C) Several big ones
D) It’s constant upkeep

5. Are property taxes or insurance premiums rising in your area?
A) Not noticeably
B) A little
C) Yes, and I feel it
D) It’s making things unaffordable

6. Are you emotionally tied to the property?
A) Yes, it’s part of my long-term plan
B) A little, but I’m practical
C) Not much
D) Not at all

7. Do you know what your property is worth in today’s market?
A) Yes, I keep close tabs
B) I have a general idea
C) Not really
D) No clue

8. Would you reinvest the proceeds elsewhere if you sold?
A) No, I’m not looking to sell
B) Maybe
C) Probably
D) Yes, I already have ideas

9. Are you tired of dealing with tenants, repairs, or management issues?
A) No
B) Occasionally
C) Definitely
D) I’m over it

10. Would you like to speak to a local expert who can give you a market value estimate and discuss your options?
A) Not right now
B) I might be open
C) Yes – I need some advice
D) Definitely – I want someone I can trust

 Score Breakdown:

Total Points: out of 40

  • 10–19 points: Hold steady.
    Your property is still performing, and your stress levels are low. With good management, this investment can continue to work for you.
  • 20–29 points: Time to review.
    You’re seeing signs of wear—financial, emotional, or both. A consultation could reveal whether selling or switching strategies is your next best step.
  • 30–40 points: Exit might be the best move.
    The numbers, the stress, or both may no longer be in your favor. Selling now could help you reallocate your energy and capital. A local expert can help you run the numbers and make the cleanest break.

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Anne-Marie McCormack
Anne-Marie McCormack

Anne-Marie McCormack has been a licensed Florida Real Estate Broker since 1996 and has worked as a licensed real estate agent in property management, rentals, and residential sales throughout Kissimmee, Davenport, Orlando, and the surrounding Central Florida communities since 1991.

As the head of McCormack Realty & Renters Choice Homes, Anne-Marie brings more than three decades of hands-on experience working with residential homeowners, investors, vacation-home owners, and out-of-state clients.

From 1994 to 2004, Anne-Marie owned and operated a successful short-term rental and property management company. This first-hand experience gives her a valuable understanding of the opportunities and challenges involved in owning and managing vacation homes, also known as holiday lets.

Today, McCormack Realty & Renters Choice Homes specializes in long-term property management and the sale of residential homes, investment properties, and vacation homes. Anne-Marie and her team also help vacation-rental owners explore whether converting their properties into long-term rentals may offer greater stability and fewer day-to-day demands.

With extensive local knowledge and a practical, straightforward approach, Anne-Marie remains committed to helping property owners protect their investments and make informed decisions about renting, managing, or selling their Central Florida homes.

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