Plenty of people are happy they took those kinds of risks.

Investing in single-family residence fix-and-flip projects in New York involves purchasing distressed or undervalued single-family homes, renovating them, and selling them at a profit.

How would you manage risk? 

A risk with lowballing is another investor comes in with a reasonable offer around the same time and Seller doesn't even want to ask you for another offer.

Your credit at risk and might affect your ability to buy a home in the future. 

Make sure every dime is deposited into the trust account.Private lending, like syndication investing, doesn’t involve many transactions.

You mentioned the risk of an unsuccessful flip.

This is what I am encountering, in the current Mortgage Industry.If you think you will go FHA, Conventional, FHA 203k, etc. and then Quit Claim the property, to a LLC, or a Land Trust you run the risk of the lender discovering a Title Transfer occurred and activating the "Acceleration Clause" or "Due on Sale Clause" that requires the loan to be paid in full, within 'x' number of days.

This one was strange because I ended up splitting the companies and partners involved in the deal so we liquidated halfway through the project. 

To have a successful STR I HIGHLY recommend listening to this episode of a podcast: https://podcasts.apple.com/us/podcast/on-the-market/id161508...Once you listen to this, and any highly involved STR operator will agree, you will find a lot of the fundamentals are lacking in Kissimmee or you have to have deep pockets to hit those.I won't spoil the episode, but if you listen to it (and anyone out there that does) feel free to DM me afterward and I'd be happy to talk details tailored to your situation on if you're on the right path or maybe I can help.