That said time in the market usually heals all wounds.

I wound up taking a loss for 2023 due to a unprofitable part of my Amazon business, and I feel like I am at a crossroads going forward.Currently, I have 400K equity in my home, and 100K in personal/business debt (and that's no one's fault but mine).

I physically tossed a colleague out of my office and I wound up in court over it. 

In the one friend with 1 rental property and his own business in example mentioned with a CPA he wound up getting audited and having to pay penalties and back taxes.

I wound recommend Wayfair to purchase large pieces of furniture...definitely NOT Walmart! 

We wound up having to replace our sewer line on our primary residence.

It may have taken me 5 months to close my first deal - but I wound up closing 6 in the next two months & I knew at the end of the school year it was time to take the jump - to become a realtor full time.I'll spare you guys the rest of the story but it's been incredible... just some of the feats I've accomplished are:1.

If you did intend to hold it as a rental but wound up selling it, you could make a case for it to be a sale subject to capital gains tax and not a flip subject to ordinary rates + self-employment tax. 

Time heals all wounds :-) Ya pay for it now or ya pay for it later, but gravity works and real estate is all about how gravity works.

None of the syndicator deals, even the best of them, wound up having enough upside to compensate for the risk of having zero control of the investment once the money leaves your bank account.