Best thing is to call the housing authority that manages the voucher program in your city/county.

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. 

Real estate transactions with non-profit organizations like nursing homes or religious entities can indeed be unique, but they’re often manageable with the right approach.

Yup, property condition, vintage, neighborhood, tenant base, property management are all very important considerations. 

Do you have a property management company you use? 

Do it very intentionally, not just for the sake of scaling up, but to get better quality or easier to manage properties that will replace lower quality or harder properties. 

Start with a good property manager.  

Allocate equity based on contributions: you provide the $235K HELOC and management, while your former boss contributes renovation expertise and labor.

Then rent the bigger home out using a property manager, allowing her to possibly cash flow and maintain that asset and let it continue to grow in value.Encourage her to consult with a CPA or tax attorney to explore the best strategy tailored to her situation.

I am licensed agent but work for an investor doing grounds management.