I know it isn't a sexy point of view, but for the majority of real estate investors, I would recommend keeping your day job and invest in real estate on the side. Real estate should complement your lifestyle, but not be your lifestyle. That might sound funny coming from a guy who obviously tried to 'Empire Build' with 92 properties and 240 doors in his career, but that is exactly the reason I am offering this advice.
There were a ton of ups and downs over the last 20 years for me. Many times I was rich on paper, but had troubles finding the cash to deal with day to day living. NONE of the major strategies offer regular cash flow over the first many years of investing. Let's review the major strategies and how likely they are to allow you to quit your day job and become a full time real estate investor.
Long term rentals or BRRRR: Let's say you find a rental property that cash flows $500 a month (which is very, very good and not that common). How many of those buildings would you need to replace your current salary? How much would it cost to buy all those properties? Let's assume you need 20% to 25% down, most likely to get in. Do you have that much money? Probably not, which means you need Joint Venture partners. Now other hands are reaching out, wanting their share of the cash flow, which means more doors are required. That also doesn't factor in the initial amount needed for renovations, and subsequent upgrades every five years or so. A much safer route is to keep your day job and acquire a few properties on your own, bit by bit, looking to augment your salary sometime down the line. A regular source of income also allows you to ride out the occasional vacancy much more easily.
Flips / Development / Condo Conversions / New Construction: These strategies are all similar in that they have money going out the door, money going out the door, money going out the door, and then finally you make a sale and some money comes back. Trust me when I tell you these strategies are horrible for predictable cash flow. Without the safety net of a regular salary this can lead to a lot of stress, especially when construction costs are more than you anticipated or things take longer to build or the finished product doesn't sell as quickly as you thought.
A lot of people look at my history as a full time real estate investor and think that is something to aspire too. What a cool life that would be? I certainly have a lot of stories to tell. However, there was WAY too much stress involved. There were long periods of time when no money was coming in, when projects were delayed or over budget, and you are wondering how groceries are going to be paid this week. Then something sells or refinances and you have some cash again.
Everybody's experience will be different, but I would suggest, for most people, go live your life, enjoy your family, and invest in real estate not as your main source of income. Real estate is a great way to get rich slowly. I know that is not very sexy, but it will allow you to sleep much better at night.
For advice on how to increase cash flow with your real estate investments check out my book on "Cash Management in Real Estate Investment"
For advice on which strategy might suit you best check out my book on "Comparing Real Estate Strategies"
Or you can always contact me directly and "Book a Chat"