The eviction process took two to three months, during which tenants would exploit the system to live rent-free.In short, the second-best day of my early investment career was purchasing that property.

The large metros areas that I've worked in like San Antonio, Fort Worth, its difficult getting answers from the decision makers. 

This should not be difficult to insure if you have the right agent/agency

As a best practice, I would absolutely recommend having some type of written lease arrangement and not have a verbal agreement as that can make it more difficult to evict and open the door for he-said, she-said arguments.If you have not considered already, I may also recommend looking into investing with Trusts and LLCs to have asset protection and/or anonymity with your personal residence and/or other investment properties.Note: This information is for educational and informational purposes only and does not constitute legal, tax, financial, or investment advice.

There's a lot of factors that influence owner occupancy purchases beyond simply the economics so its difficult to say there is a right decision.

The properties below $100k will be difficult to finance on a portfolio since most lenders are valuing each asset individually (not the entire portfolio) You may want to try a local commercial bank first to see if they are able to value the entire portfolio, not individually. 

That could be a negotiation point as well--we can settle this outside of court and collections so you don't have a public record to make it more difficult to rent in the future. 

Even if I successfully lease the property to a new tenant, I worry the current tenant might refuse to vacate after their lease expires, potentially leading to a difficult eviction process and jeopardizing the new lease agreement.Given these complexities – the tenant's refusal based on a non-occupant's health, the potential underlying motivation, my need to show the property, and the risk of a holdover – I would greatly appreciate any advice, strategies, or insights on the following:1. 

Quote from @Michael Baum: Hey @Katie Accashian, so you are buying a place in an area that is known to be difficult to do STRs in.

I do not have any prior experience investing in NYC, so my question to you all is:- How difficult is it to evict tenants that are behind on rent?