It’s obviously livable since they have tenants in all 4 units so it can’t be that bad I guess?

The more you do this, the faster you’ll recognize a good (or bad) deal. 

That being said the options you listed seem pretty bad.

Main risk is rehab going over or low appraisal so make sure you do the current due diligence. 1 is not a bad thing but a slower way to go. 

Bringing in a local real estate attorney familiar with NYC housing laws wouldn’t be a bad idea either moving forward. 

Least you learned now, not after making more bad buys.

This is a bad RE investment.  

My current agent doesn't offer this, Steadily had so many bad reviews I wouldnt consider them, and NREIG doesn't cover named storms (it being hurricane season in Houston that's not an option).  

Working for free is not a bad option if you cannot get a paid job in the real estate world, because once they see you are determined and dependable, they will figure out a way to pay you to keep you.You said you've tried to get a job in property management, property development, and similar fields.

If you're getting strategy + bookkeeping + prep, that's probably not a bad deal.