Couple other things to consider, property / school taxes are high, and tenants have lots of rights.

I won't just write them all here but I highly recommend contacting a qualified 1031 intermediary to walk you through the process.

90% is pretty high.

If you rent in a high-crime area, I wouldn't suggest it.

But the answer for everyone may differ.Here are the personal attributes I see in those able to achieve a higher than market ROI, enough higher to be able to “scale”.1- Knowledge of real estate principles, real estate law and real estate finance2- Minimum 3 -5 years full time, or near full time experience directly related to real estate investing3- Ability to utilize technology for increased efficiency, capacity, and accuracy4- Excellent hired legal counsel and excellent hired marketing help5- Established method(s) of obtaining consistently high QUALITY deal flow6- Ability to manage and choose people who are NOT employees: Attorneys, Appraisers, Mortgage Brokers, Real Estate Brokers, Title Companies, Surveyors, Marketing Specialists, Accountants, Contractors, Consultants, Property Managers7- A VERIFIABLE track record of success8- Ability to identify, analyze, and negotiate a deal that can be “worked” for “enhanced” ROI9- Some type of competitive advantage; for example for me it’s my ability to analyze and identify mortgage loans that are actually less risky than all other lenders believe (on the investing in debt side), and on the real property side it’s my ability to analyze”pull the trigger” with LESS information than other investors need,  combined with the ability to pay cash, or raise significant capital almost instantly as well as being able to obtain loans at the lowest prime customer bank rate with no recourse or personal liability.  

If prices are too high people will just go elsewhere.

If you want to quote out high efficiency boilers for six Tripple deckers for example requiring installation of separate gas, meters etc. etc. - that might be a situation where you would want to work with a contractor directly because you would have lots of different options with widely varying costs.

If you have large debt with a high interest rate, I would consider paying that off before getting started investing in real estate. 

I'm in New York but the prices (at least downstate) are much too high for me to make my first deal so looking more upstate and out of state. 

we are pretty high that is for sure.