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Spring Cleaning Checklist for Real Estate Investors

Written by Tyler C. Gates

Published 05/07/2025

Winter in New England is great if you love snow and find yourself busy with winter activities. If you don’t enjoy the cold or the snow, you may find yourself keeping busy with work or indoor activities. 


Just as the sun comes up every day and the moon each night, the winter eventually turns to spring. With this change of seasons we find ourselves cleaning out our homes, cars, offices as well as many other aspects of our lives.


Why not then as landlords, follow a similar spring cleaning checklist each year to declutter our lives and make sure the rest of the year is set up for success.


Spring Cleaning Checklist for Real Estate Investors

The goal of spring cleaning as I alluded to above is to declutter and to simplify our lives. If at any point it feels like work or is adding to your future workload, stop and reevaluate. 


Now that you have permission to walk away at any time, let's look at the five things I believe all investors should do or have done by a property management team every year.


Walk Your Properties

Map Out the Year

Rough Cash Flow Analysis

Check in With Network

Revisit Goals, Adjust if Necessary


Checklist Item #1 - Walk your Properties

It sounds like a given but you would be shocked how many investors I know around town don’t visit their properties. The majority of tenants we have had are willing to speak up if something happens but 9/10 of them are not looking at the property like you as the owner would. 


Is there any visible water damage or siding damage from the winter months?

Are the trees healthy and coming back to life or should any be dropped before next winter?

Any foundation work that needs to be done?

What about the roof, or the chimney, or the trim work?

Water heater, furnace, boiler or other systems all serviced and in good shape?


Likely you and only you are going to be the one to spot these critical items. Walk with a clipboard and rank every item you see on a scale of 1-5 or 1-10, whatever floats your boat… 


Do this first before you move on to any other Checklist item. It is important to do these steps in order to save yourself time and headache in the long run. I only speak from experience.


Checklist Item #2 - Map Out the Year

With the knowledge you recently acquired from your property arounds, it is time to map out the major events for the year ahead. I am not talking about trying to budget for your electric bill or your water bills here. I am referring to the big ticket items including capital updates (from Checklist Item #1), taxes, insurance bills, balloon payments, rent increases, turnovers, etc.


An example may be helpful, our list for three properties/thirteen units looks a little like this - 


May - 

  1. Walk Properties

  2. Property #1 - Yearly Insurance Payment Due


June - 

  1. Q2 NNN Bills - Properties #1 & #2

  2. Salon Rent Increases by $100


July - 

  1. Property #1, Unit 1 - Send 60 Day Renewal Notice

  2. Property #1, #2 & #3 - Semi Annual Taxes Due


August -

  1. Property #3 - Rebuild Exterior Deck & Trim Work

  2. Property #1, Unit 3 - Send 60 Day Renewal Notice

  3. Property #2, Unit 1 & 2 - Send 60 Day Renewal Notice


September - 

  1. Q3 NNN Bills - Properties #1 & #2


October - 

  1. Property #1, Unit 2 - Turnover Unit (30 Days or Less)

  2. Property #2 & #3 - Semi Annual Insurance Payment


November - 

  1. Yearly Plow Contract Payment Due


December - 

  1. Q4 NNN Bills - Properties #1 & #2


Take whatever list you make and add them to your calendar or find a way to set yourself a reminder on specific dates so after today, you don't have to think about this list again until your phone dings or your reminder goes off!


Checklist Item #3 - Rough Cash Flow Analysis

Now that you’ve got your major milestones out of the way, let's see if we will have enough cash to bring our vision to life.


To do this, you can do a rough back of the napkin calculation but for me this number is a number you should know everyday of every year. If you feel the same, take a few minutes to build a spreadsheet that suits what you’re trying to accomplish. For us, we want to know what is our Net Operating Income*** (See Table at the Bottom)


You may disagree with what we track and thats the beauty of it, build a template that fits your needs! If a napkin is all you need to do some quick math for the year, go grab a coffee or beer and get this thing done.


Checklist Item #4 - Check in With Network

Congratulations! If you’ve made it this far, you’ve completed the hard work and now we get to relax a bit. Just think, by now you have walked your properties, added all the major milestones for the year ahead to your calendar, analized your cash position and found out not only what is possible but what is probable. 


As we come out from the winter slumps here in New England, others do the same. Now is the best time to call your electrician and see how they are doing? See if you have work this year what time of year may work best for them and keep that in mind.


Call your carpenter and let them know that when you were walking your property you noticed some trim rot and that one of the side decks needs replacing. Let them know that this is not an emergency but you just wanted to say hi and that you've budget for this to be done sometime before year end. 


Call your accountant and say thank you for getting you and their other clients through tax time and see if there is any reason for you to come in when times are slower to do any additional tax planning for the year ahead.


This is the time to simply be friendly, you don't need anything right away, just saying hello and putting your projects on their radar at most! This will go a long way when you need them. You will be shocked how many times they call you back before you need them to see if you need anything when they have a few days of work free up.


Checklist Item #5 - Revisit Goals, Adjust if Necessary

Maybe you set out the year with a goal to buy another building, to increase revenues by 9% or decrease expenditures by 4%. Now is a great time to revisit these goals and expectations you set for yourself and compare them to not only where you are today but to your yearly map and information gathered from the Checklist Items above.


If you need to change course of action to reach your goals, do it while you have time on your side and not in December when you start to pull your books together. 


I would love to see you change your plans on how you achieve your goal instead of changing your goal because you didn't do the proper planning.


Spring is here, knock out this Checklist and feel great about the months to come!

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