Financially free always betas debt free, and taking on more "smart" debt is not only opposite of risky but actually the goal for the most seasonal investors.  

. - When we've review these options with clients the ending outcome is typically that it's easier to forgo the 121 exclusion if you want to keep this property; and do a cash-out refinance (taking on more debt isn't taxable) instead. 

Also, the home owner most likely has a mortgage and receiving a large amount of cash and then not spending it for 3 months can be more challenging than you’d think.

You may also have to get your "hands dirty" in order to make these properties cash flow.

If the property cash flow starts in 2024, personal usage is not that impactful.Talk to your CPA if renovation counts as QIP for bonus depreciation.

Use the HELOC on cash-generating opportunities like flips, then use the cash generated to buy long-term buy and hold investments. 

Couple this with the "Cash Distributions from Capital Transactions" clause and you begin to see the real problem.

There are ways to invest in real estate without using your own cash upfront.

So about a 35% cash on cash return for my buddy each year on his $100,000.

The school is very good, but middle is not so much.I have some cash to invest, but can't decide what route to take.