I have posted quite a bit on this topic, so I will refrain from expounding again.If you need guidance on the specifics of navigating NY's draconian L/T laws, feel free to reach out.

Also looking for recommendations on a CPA that can help me navigate the renovation and rental. 

House hack a multi-family property - when you've comfortably navigated the prior steps to a reasonable level, I would look to get approved for a loan to house hack a MFH.

They often allow you to attend one member meeting free before joining and you might actually be able to make enough contacts that once to make a difference.Someone else can better help you navigate finding a landing place to buy.  

Ambulance chasing attorneys know their way around and can legally navigate around Insurance Policies.

You can work with a professional to create a structure that puts you very much in control of the investing, but always want to have someone on your team who can help you to navigate the IRS rules.For investments like rental properties that tend to involve a lot of transactions, some of which may be time-sensitive, there will be significant benefits with a plan that offers checkbook control such as an IRA LLC or - if you qualify as self-employed with no full time employees - a Solo 401(k).  

Usually, the first option for getting Virtual Assistants is Fiverr or Upwork since they're both easy to navigate and hiring can be done in an instant.

Should I talk to a real estate lawyer or to a CPA/lawyer to help me navigate the complexity of this transfer?

I am a US expat living in Japan, which means I have the difficult task of navigating both US and Japanese taxes and laws.

I know he could help you navigate your situation.Best of luck to you!