In both cases I settled with the homeowner to avoid aggravation, lost time, and expensive lawyers.

One year ago, I was hired to help a landlord whose tenant had stopped paying.

maybe several times.  

Purchase price: $325,000 Cash invested: $50,000 This time I acquired a property that needed little to no work.

We are a long-time partner and supporter of the BP community.

@Denis Orlov I don't do STR, but I've rented one of my personal properties for arbitrage before. 

They will give you a few minutes of their time and tell you if their products are right for you.

I'll also add that guidelines change over time. just because they don't like it now doesnt mean they wont decide later to be okay with it.  

I have a tenant in one of my units who has filed for chapter 7 bankruptcy.

Since you're open to markets beyond NYC, you might want to connect with local investor meetups or REI groups in those areas to build relationships with agents, wholesalers, and lenders who understand the nuances of each market.If you're looking to break out of analysis paralysis, maybe start by narrowing down one or two target markets and running numbers on actual deals.