The responsible time to begin raising capital is once you’ve taken projects through full life cycles (hopefully some with success). 

Don’t copy their design make your own but look at styles that work, what can you do that makes you special, can you do a theme that will stand out? 

Based in New York, my work-life spans across New York City and Long Island while I reside in Mount Vernon, Westchester County.I’m diving deep into real estate investing, working on building my knowledge first and my portfolio later.

You are talking spreadsheet language in the post that doesn't really correlate to real life unless you are very experienced and using this data based on your experience.

People sometimes make bad decisions in life and you have to decide whether it is forgivable or not.

Edit: And taking 10-20% equity on a deal like this with an experienced investor might be completely worthwhile and life changing to be clear. 

It's one of those things that you just have to keep on keepin on because at the end of the day, it only takes one seller to change your life.

It's not "our" conversation and I personally love your insights, whether I agree with them or not.You know I think you've created your own mix of lifestyle/investment purchase.

Some people just don't have good mentors in there life, and/or need to learn through mistake.

You can still find some great cottage style homes or even 2-4 units close to the beach that have great STR returns.One good thing about being out of state in IL is you can find a good Single family home, Condo, or Townhome and call it a Vacation home and only need 10% down.