Best way to generate cashflow with $400,000

[Ryan D.]

I am seeking input from experienced MF investors. Seeking advice on best way to get started with $450,000 in savings and $100,000 in home equity.

My name is Ryan. My wife and I are looking to get back into real estate investment after a disastrous experience during the 2008 meltdown. We had nightmare property management problems from a distance and lost about $45k between a SF and our duplex. Needless to say we are a little gun shy. We are also in a slightly unusual situation. Neither of us have a W2 job. My wife is a stay at home mom and homeschools our 4 kids. I started a business in 2018 and have faced several speed bumps along the way, so am not yet taking any income from the business, although it has a lot of potential. We took a risk given the potential reward of the business and have been living off of our savings and IRA. Unfortunately, due to supply chain issues due to Covid the business potential profitability has been greatly reduced recently so I am exploring whether I should put all my effort into real estate investing instead.

Additionally, one of the hurdles we faced the last few years is that my wife has metastatic breast cancer in her brain. As a result we were able to collect an early death benefit on her life insurance and now have about $450,000 in savings (currently invested in the stock market and bonds), plus about $100,000 of equity in our home. We would like to invest this money to generate cash flow, and grow our equity over time, but are struggling to narrow down the multitude of options. We also have to be somewhat careful with this money as it is supposed to be there if my wife dies to help support the kids.

We live in a rural area of southwest Wisconsin, although we are just outside Platteville which is a small college town (pop.~12,000). We could probably find some local properties that cashflow well, but Wisconsin's rural counties are all projected to have near zero, to negative, population growth from 2020-2030. Seems risky to me. We are primarily looking at either larger college towns (pop.>60,000), or Midwest cities that have experienced sustained growth such as Des Moines, IA, Madison, WI, etc. 

Our long term interest is to get into larger multifamily (10-20+ units), but concerned that putting all the money into one larger building as our first investment might be too risky. Alternatively, spreading it out over multiple smaller SF/Duplex/Triplex/Quads would allow us to ease our way into it, but would also slow us down from just getting to the larger buildings we are ultimately interested in. Also, my prior experience was that it was difficult to get a property manager for only one or two smaller properties, whereas, it is much easier to get a manager for a 10-20 unit building. 

So many people say get started small, others say just go big from the start. Any advice from experienced investors as to how to get started?

Sorry for the long post.