Massachusetts Crash Course in Landlording and Rental Real Estate

This crash course in landlording teaches everything you need to succeed as an owner or manager of residential rental real estate in Massachusetts. Below you will find a full outline of our highly rated crash course or "landlording 101." This course is designed for buy-and-hold real estate investors. This course does not teach flipping or other "get rich quick" systems.

massachuetts crash course in landlording and rental real estate instructor and attendees in cambridge and example crash course certificate

This fast-paced course is strictly limited to 16 participants to allow for detailed discussion and Q&A.

Course tuition includes:

  • Small group session with the Executive Director, a trained presenter and experienced landlord, and/or an attorney, depending on location.
  • A comprehensive agenda, see below.
  • Your choice of two books:
    • Every Landlord's Tax Deduction Guide by NOLO,
    • The Good Landlord by Peter Shapiro,
    • Getting to Yes by Roger Fisher, and/or
    • The Property Management Manual by H. John Fisher.
  • A bound summary of all material presented.
  • A MassLandlords ballpoint pen.
  • A coupon for 10% off any MassLandlords annual membership.
  • A MassLandlords certificate of completion and permission to use "MassLandlords Crash Course graduate" on your marketing material.

Course Features:

  • For small and large owners, managers and undecided.
  • Ask our attorney anything.
  • Highly rated.
  • Feel confident you can succeed!

Each course also features both a landlord and an attorney. Here is the current instructor roster:

Instructor and Attorney Adam Sherwin

Instructor and Attorney Adam Sherwin

Instructor and Landlord Douglas Quattrochi

Instructor and Landlord Douglas Quattrochi

Instructor and Attorney Peter Vickery

Instructor and Attorney Peter Vickery

Crash Course Date Public Ticket Member Ticket
Cambridge Crash Course - Sat April 13
The MassLandlords Crash Course in Landlording: Give Your Business a Spring Cleaning
$275 $250
Member? Log in.
No events? Not at the right time?
Join our mailing list to be notified when new dates become available.


Course Graduate Testimonials

Celebrating 500 Crash Course Graduates and selected testimonials.

“I simply wanted to reach out and express just how happy I am to have attended the landlording crash course instructed by Doug. The presentation and delivery of the information was flawless and I certainly have walked away with a greater understanding of the intricacies that govern being an above average landlord/manager. I hope MassLandlords continues to provide its members and the Worcester communities with resources that will further advance its development. Keep up the great work and thank you again!” – Michael Murray
“Mr. Quattrochi presented the course in a comprehensive and easy to follow step-by-step format. His PowerPoint presentation was provided to us, in a binder, as part of the course, and I took notes right on the pages. I find this part to be an effective tool because I can refer to it anytime I need to follow procedure. There’s more to it, but for a fun day, I personally, recommend this course to anyone in the Real Estate landlording/investing business, beginners in this profession as well as experience professionals.” – Edwin Rivera

"This has really been a great deal. 2 books, 8 hours 'class' time, bound notes/slides -- impressive value!" -Dawn

"I found this course extremely useful. It was completely professional and gave me a great new perspective." -Nicholas

"I’m glad there was more in depth discussion than just reading off the slides. I appreciate the opportunity for questions and practice." -Crash Course Graduate

"If I had done this 20 years ago. Oh my goodness!" -Crash Course Graduate

"Great overview of being a landlord in MA" -Crash Course Graduate

"Covered a lot of ground concisely, but still enough time for questions and insight. Worth every penny." -Crash Course Graduate

This Course is Given In-person or Virtually

Depending on the event you select, this will be either in-person or virtual. The curriculum is exactly the same. It's only a question of your preference for in-person or virtual.

If Virtual, Agenda

When held virtually, our comprehensive training is split over two days to reduce screen time.

Day One

  • 8:30 am - Introduction of MassLandlords and course participants
  • 8:50 - Rental markets
    • Urban, suburban, rural
    • Luxury, college, professional, working, subsidized, rooming houses
  • 9:05 - Property selection
    • Lead paint (Legal highlight)
    • Utilities
    • Bones vs surfaces
    • Amenities
    • Repairs and renovations
    • Durable vs beautiful
    • What if I'm stuck with what I've got?
  • 9:20 - Sales and marketing 101 for rental property managers
    • Marketing rentals
    • Sales process
    • Staying organized
    • Branding a small business
    • Getting more or fewer calls
    • Tips and tricks
  • 10:05 - Break
  • 10:15 - Applications and screening
    • Criminal, credit, eviction
    • Discrimination (legal highlight)
    • Tenant Screening Workshop
  • 11:20 - If time allows, start Rental Forms
    • Lease vs Tenancy at Will
    • iCORI
    • Eviction notices
  • 12:15 - End Day One, course resumes the following Saturday

Day Two

  • 8:30 - Review of Day One and follow-up questions
  • 8:45 - If needed, finish Rental Forms
    • Lease vs Tenancy at Will
    • iCORI
    • Eviction notices
  • 9:15 - Legal Matters start
    • Late fees
    • Security deposits
    • Eviction process
    • Move-and-store
    • Water and electrical submetering
    • Housing Court vs District Court
    • Warranty of habitability
    • Inspections
    • Subsidies
    • Rent control
  • 10:05 - Break
  • 10:15 - Legal Matters finish
  • 11:00 - Maintenance, hiring, and operations
    • Keeping the rent roll and expenses
    • Filing taxes
    • To manage or not to manage
    • Tenants as customers
    • Notifying tenants
    • Extermination
    • Monitoring contractors
    • Lease violations and conflict resolution
    • Record keeping
  • 11:50 - Overview of books and resources for further education
  • 12:00 - Review of unanswered questions
  • 12:15 - End Day Two and End Course

Please note that end time each day may vary based on questions.

If In-Person, Agenda

When held in person, our course takes a single day.

  • 8:30 am - Introduction of MassLandlords and course participants
  • 8:45 - Rental markets
    • Urban, suburban, rural.
    • Luxury, college, professional, working, subsidized, rooming houses.
    • Airbnb.
  • 9:00 - Property selection
    • Lead paint.
    • Charging for utilities.
    • Climate change risk.
    • Heat pumps.
    • Vinyl plank vs. hardwood floors.
    • Landlord trade-offs repairs vs. cleaning.
  • 9:40 - Marketing and advertising
    • Getting the right applicants.
    • Small business branding tips and tricks.
    • Where to advertise.
  • 10:05 - Break for ten minutes
  • 10:15 - Finish marketing and advertising
  • 10:35 - Applications and tenant screening
    • Criminal, credit, and eviction background checks.
    • Discrimination and fair housing.
    • Interactive tenant screening workshop.
    • Section 8.
  • 11:30 - Tenancies
    • Lease vs Tenancy at Will.
    • Move-in monies.
    • Security deposits.
    • Pet rent.
  • 11:50 - Break and Lunch, with free form Q&A
  • 12:20 - Warranties and covenants
    • Water submetering.
    • Sanitary code.
    • How to raise the rent fairly.
    • Support animals.
  • 12:40 - Dispute resolution
    • Eviction notices to quit.
    • Court process.
    • Move-and-store
    • Relocation assistance.
  • 1:40 - Break for ten minutes
  • 2:50 - Maintenance, hiring, and operations.
    • Tax advantages.
    • Property managers.
    • Contractors.
    • Building permits.
    • Extermination
    • LLCs and trusts.
    • Grants and alternative funding.
  • 3:10 - Break for five minutes
  • 3:40 - Overview of books and resources for further education
  • 3:45 - Review of unanswered questions
  • 4:00 - End Course

Please note that end time may vary based on questions.

Who Should Take this Crash Course

This real estate training is designed for all hands-on operators. Whether you are a non-landlord considering making your first investment or a manager with decades of experience over hundreds of units, we will address your particular learning objectives. Each course starts by collecting a list of goals from participants and we hit every one. Business purchasers: We are happy to train new employees who need to get up to speed quickly and family members learning the trade or taking over the business. Our registration process automatically prompts to ask if attendee names will be different from the purchaser's name.

Do not sign up for this course if you only want to learn how to flip houses, invest in foreclosures, or be a hands-off investor. We're happy to talk to you about those things, but that is not this course. This course is operations-heavy. See agenda.

Food when virtual

When selecting a virtual course, note that you will be free to prepare food at home and eat while you listen. Or eat before and after as suits your preference. We don't mind!

Food when in-person

  • Continental Breakfast
    • Fresh Baked Pastries, Muffins and Donuts
    • Variety of Bagels with Cream Cheese and Butter
    • Fresh Cut Fruit
    • Coffee
    • Tea
    • Orange Juice
  • Lunch
    • Assorted Paninis
    • Soft Drinks, ice tea, lemonade, and water

*Dietary restrictions: purchase a ticket one week in advance and email, we will accommodate you.


Open to the public. Membership is not required, but advance registration is required!

  • Public: $275
  • Members: $250

The virtual and in-person courses are the same price because our estimate of shipping and handling on a box of course materials is equal to our cost per person of catering. Virtual attendees will receive a box packed with your personalized signed certificate, your choice of two books, course notes, pen, and half a dozen other pieces of literature. In-person attendees will receive this material day-of.

Crash Course Date Public Ticket Member Ticket
Cambridge Crash Course - Sat April 13
The MassLandlords Crash Course in Landlording: Give Your Business a Spring Cleaning
$275 $250
Member? Log in.
No events? Not at the right time?
Join our mailing list to be notified when new dates become available.