Are their listings detailed with good-quality photos?

Here's a https://www.irs.gov/businesses/cost-segregation-audit-technique-guide-chapter-4-principal-elements-of-a-quality-cost-segregation-study-and-report to the IRS website noting specific items that are included in the cost segregation study report. hmm, that website is a 404 error.  

This isn't just high risk your talking about Zach, your talking about compounded high risk. 

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

In North Jersey, buying is difficult from my beginner perspective with high prices, property tax, etc.Barrier to entry feels high in my area.

Once you narrow it down, start with small jobs to test their reliability and quality before giving them bigger projects.Building a solid network takes time, but having dependable people on call is a lifesaver for your rentals.

@Sakib KhanRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I have a second condo property where the water quality became unacceptable (PFAS) so I put a filter on the sink and make people aware the fridge water no longer works.

If the answer is "close enough," they move forward without much hesitation.While it's true that higher-quality tenants are easier to attract with nicer homes in better areas, I’ve managed C-class properties and had fantastic tenants.

You get so much wealth and start getting older you enjoy the business but focus on quality of life more and memories.