To avoid that, set a firm, realistic budget from the beginning and make sure you stick to it.

Here is a video that runs down the basics - https://s-media.nyc.gov/agencies/specialenforcement/01-Legal...There is also a prohibited building list - https://www.nyc.gov/site/specialenforcement/registration-law...Here are some more info overall - https://www.nyc.gov/site/specialenforcement/registration-law..All of this makes STRs in the city pretty tough but it certainly not impossible.

If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

Lastly, there's very landlord friendly laws here!

I would think their loan documents give them the right to control the property after the original owner dies - regardless of who is living there (although I have no direct knowledge of the laws where you live).There are details we don't know here... like if you want the house for sentimental reasons, or because you see the value between what it's worth on the market today and what the reverse mortgage company wants for it?  

I'm currently working with an estate planning attorney and she said she said we could put the LLC in the Trust but said she was not the best person to advise on the pros and cons of that and that we should talk to a business law attorney.

STR is another concern, many towns have laws against it but most towns do not enforce these laws, just make sure you are aware of them becuase they can be enforced. 

I'm a Project Manager at an Architectural Firm specializing in Custom High-End Homes. 

You need to really learn these laws if you want to start a partnership where you make the decisions.

Business is good and we have a new law in PA that a Wholesaler has to be a licensed Real Estate Agent.