You could form a Joint Venture Specific LLC and have a good real estate attorney draft an iron-clad Operating Agreement to minimize your risks, limit liability, and protect your personal assets all at once.

Remember your time is worth something and you are taking the risk.  

Maybe, spread the risk.

Also, there could be a risk of missing some transactions if you're relying on receipts. 

I can see the upsides of no debt and a lot less risk, with higher Cash flow every month but not sure if this is a mistake and I should take the money I have and try to buy a couple places at the same time and finance them. looking for advise from experienced investors out there. 

With self-directed IRA the sky is the limit.Of course you must be aware of the IRS prohibited transactions and be sure to stay away from those:https://www.irs.gov/retirement-plans/plan-particip...Selecting appropriate investment option depends on many different factors such as your age and investment horizon, your risk tolerance, investment experience, etc.

Too many other ways to make more money safely.Go into real estate investing to be profitable, with low risk, having fun.

There are many perks that can reduce your risk, and if there's ever a problem with your tenant, you just walk next door.

In this way they get the benefit of the safety of cash still getting good returns and the potential bounce from strong leverage but concentrated in fewer properties so risk is less.The other issue is the desire to wind it down. 

There are no tail winds to speak of to carry you through bad decisions, but good cash flow opportunities exist.