We all have that one friend that has been talking about buying their first house for longer than we can remember. Being an investor, I hear so many people talking about getting into Real Estate but don’t know if now is the right time. 

The truth is, there is never a perfect time. 

One of the best financial quotes I have heard came from a Partner at Edward Jones who said something along the lines of, "the best time to buy is when you have the money available”.

If we were to look all the way back past the housing crisis in 2008, returns would look so good even with this event that you almost wouldn't believe me. To make it feel more real, let's look at life since COVID 19 or roughly the last five years.

Over this time, Residential 30 Year fixed rates started to fall in 2019 from 4% to as low as the mid 2%’s by Q4 2020. Rates almost immediately started climbing and peaked as high as 7% in late 2023 and early 2024.

Since 2020, our government has added $13,000,000,000,000 in debt to our massive IOU bringing the debt total to roughly 36.2 Trillion Dollars as of June, 2025.

Fear has a way of stopping people from taking action, myself included. So let's look objectively at what has happened in Real Estate over that time. Let's start with Residential Real Estate. 

Residential Real Estate - 

For this section, we will look at a few places my wife and I have lived so please keep in mind this blog will be very North East focused.

New Hampshire has seen an increase in home prices month over month since 2019. On the flip side, reports show that monthly payments for an average home have jumped over 150% during that same period. 

Massachusetts has seen a significant bump above and beyond their average 3-4% a year appreciation as much of the US has. NCHStats estimates that from 2019 to 2024, Residential Home Values jumped a tick above 9% a year adding 45% in value to home owners that bought and held during that time frame.

Maine has been no different seeing over 50% growth over the last five years while income and wage growth only kept pace at roughly 30%.

Some of this sounds like bubble territory. At the very least, some of this sounds like we may be at the end of a good run. That I do not know and will not even pretend to try!

What I do know is if you have the money available, you’re comfortable with your monthly payments, have an emergency fund set aside and feel good about your ability to earn income into the future (W2 Work/Self Employed/Business Owner, Etc) then I am a big believer in buying NOW.

If you’re considering a 2-4 family which you should be, planning for who may and may not pay in times of trouble are just as important as thinking about your own ability to earn. Vetting properly on the front end can save you time and money in the long run. 

Commercial Real Estate

It has been harder to spot trends online for entire States as Commercial Real Estate can differ dramatically from town to town, city to city.

Conway, NH for example has seen a growth rate continue to hover in this space at 4-5%. This is however music to most Commercial Real Estate Investors ears as building/land appreciation is not the driving factor typically behind profits. Cash flow is king and rental rates in many towns have ballooned as much as 65% across parts of NH.

Boston, MA was hit very differently by COVID 19 then rural New Hampshire. Skyscrapers, left empty as WFH began. Although values have stayed mainly flat across the city, rental rates have increased putting more cash flow in landlords pockets to focus on building repairs, renovations and adjusting to new demands.

Portland, ME is a bit smaller of a city of course and saw modest growth over this time. Much like Boston, it is likely in stabilization mode and rental increases over the last five years have been able to support the Real Estate landscape.

We personally prefer commercial Real Estate as we have found that we have more control over Income and Expenses which ultimately drives value in this space.

Although I hoped at the beginning of this blog to use very specific numbers and analytics, it proved more challenging to produce across three states. I would encourage you to work with a seasoned Realtor or consider partnering with a seasoned investor on your first deal if you're not confident in your ability to find, fund and execute deals from start to finish.

There are awesome resources like https://www.city-data.com and https://www.neighborhoodscout.com that can help you learn more about your target areas and future properties. 

With a little hard work, you can always find a good deal that makes sense based on your current situation. Should you push yourself to the breaking point to fund a deal, absolutely not. We have done this too many times in the past and it caused a great deal of unnecessary stress.

Time In the Market VS Timing the Market? I will always choose Time In the Market.

As I stated above, if you’re comfortable with your monthly payments, have an emergency fund set aside and feel good about your ability to earn income into the future (W2 Work/Self Employed/Business Owner, Etc) then I am a big believer in buying NOW.

If you do not feel at least 95% confident in ALL of the above categories, keep at it until you do and circle back! Real Estate will always be here when you are ready. 

Just please, please, please don’t be the person who talks about how ready they are but sits on the sidelines for years while the Real Estate world passes them by.