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. 

A "lake house" might be in a residential zoned area where a commercial use would be prohibited or at least require a variance (approval) to make an exception.

The end goal is to have a piece of land with multiple houses: one for my growing family but also a home for my mother in law.My mother in law has agreed to foot the money on a new property/land up front and when ready we can buy land from her to build/develop etc. 

I think the development of the place is in the vision of the leaders.

The current price of the house is worth about $900000.

The front end can sometimes be tedious to get approved by the local housing authority, but rent payments are always timely.

I looked into this at more than one occasion, because Milwaukee has such an old housing stock, everything is 60-120 years old.Most of the new apartments we see are 4 and 5 star developments with very high rents, this allows to offset the high cost of construction a little better.

I'd guess I could sell my house with ADU for 650-675.

Just got the second house in my current partnership!  

What the city housing clerk is telling me is that there was a water leak from behind the sink pedestal on the second floor bathroom that has been running for a week.