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 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.

contractor teaching how to identify good investment property

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 Housing 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.

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

crash course instructor attorney adam sherwin
Instructor and Attorney Adam Sherwin
crash course instructor douglas quattrochi
Instructor and Landlord Douglas Quattrochi
crash course instructor attorney peter vickery
Instructor and Attorney Peter Vickery


Crash Course Date Public Ticket Member Ticket
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Course Graduate 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 (Worcester Crash Course 7/17)
“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 (Springfield Crash Course 10/16)

About the virtual course:
"This has really been a great deal. 2 books, 8 hours 'class' time, bound notes/slides -- impressive value!" -Dawn
"I’m glad there was more in depth discussion than just reading off the slides. I appreciate the opportunity for questions and practice." -Anonymous

Virtual Course Agenda

This comprehensive training is now 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.

Who Should Take this Crash Course

This real estate training is designed for experienced owners and managers who want to be brought up to date with changes and best practices, new employees who need to get up to speed quickly, and family members new to the business or planning to take it over at some point.

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.


This is a virtual course. You are free to prepare food at home and eat while you listen.


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

  • Public: $215
  • Members: $205

The course is the same price as usual, because our estimate of shipping and handling on a box of course materials is equal to our historic cost per person of catering. You 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. Materials will be mailed when the US curve flattens and we have a local team member healthy for fourteen days consecutively. Electronic course notes will be downloadable for printing at home and notetaking prior to the event.

Crash Course Date Public Ticket Member Ticket
No events? Not at the right time?
Join our mailing list to be notified when new dates become available.




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