Best method to invest in properties

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First some background.

My dad invests in properties, but does not like to carry loans on them. He currently owns 10 properties out right in Nevada, including his own home. As rent comes in, he keeps it invested in bonds until he has accrued enough to buy another home. When he was younger, he would buy fixer uppers in good neighborhoods and spend time fixing them up while also holding a full time job. I spent most of my childhood with him doing everything from painting to re roofing homes, gutting kitchens, wiring, plumbing, etc. but it has taken him years to acrue the 10 homes.

On the flip side, I have an uncle that also while holding a full time job, invests as little money as possible, but buys as many homes as possible. He past away about 10 years back, but had 5 apartment buildings and 15+ homes. He invested in California, and before the real estate crash his daughter sold everything off for huge gains.

My dad felt my uncle was foolish because he felt that when, not if the crash came, he would be secure and my uncle would loose everything.

Three years ago I was forced to sell a commercial building I owned because I broke my back and my business that occupied the building was struggling to make the high mortgage. Luckily I had a buyer that had been pestering me for two years to sell, and was a realtor herself, so I paid no fees in the sale. My property was in Silicone Valley. I took the money from that sale and purchased a new home outright in Apex, North Carolina. I still have my business in California, now in a rented building, so I commute back and forth. This year with the housing market being so good we decided to sell our home in California and we purchased our first rental property also in Apex, North Carolina, again outright. My wife and I were scared about how long it would take to rent, but put it on the market last weekend and had it rented with a one year lease the same weekend to what we hope is a great couple. We did our homework and ran credit and background checks.

I am selling my business next month to one of my employees, so I will no longer have to commute and will be getting $2687 per month for the next ten years. The only other income will be from my rental which should profit about 1k per month after expenses.

Should I follow my dads footsteps and work slowly with little chance of loosing all, or pull a HELOC against my home and try to purchase several homes with 20% down? I don't think a bank would currently give me a loan, have not tried yet, but until I can show steady income from the rental and sale of business, I figure 6 months, hopefully banks will fund me. Both my wife and I have credit scores in the high 780's so that should not be a factor.

Our home is worth $230k+ and the rental is $170k+ again, free and clear of any loans.

I really want a fixer upper to keep me busy, but my wife also wants instant oatmeal, so homes ready to be moved into.

I'm just looking ten years down the road when I no longer have that $2687 coming in each month, and know 1k per month won't cut it. We have no bills and about 45k earning pennies in the bank as well. Son just started college and daughter two years from college as well. College funds in place which should take my son thru all four years and my daughter thru first two years. She wants to go to Brown University, and is already applying for scholarships two years in advance.

Sorry for such a long story, but confused about the right approach, safety versus quantity. We are 45 and don't want to enter the job market, would rather try and enjoy our kids and life.

Thanks for any feedback.

Mike