I am at a point where I'd like to give another go at business ownership (but retain my 9-5, which I enjoy).

I have a ton of failed app/websites I've attempted, built/owned a bar, and have been brainstorming on what I would like to do next.

My current plan is to start investing in real estate (flips and multi-unit rentals) but as I think about things I see a lot of parallels with owning "digital properties". I am curious if anyone has had success (defined as growing the MoM cashflow) with buying a site from somewhere like empireflippers in the 50-100k investment range? What did the process look like? What are the risks and got yas?