It is currently a glorified finished attic with little room- Use addition and raise it up and extend it to the side of the home for more finished space and room for deck, washer/dryer room etc- Make the living space as functional as possible with the added sqft- Add outside living structures like deckThis is a fairly wealthily area and I want to maximize my ROIWhat are some things you recommend for a large scale project like this and what are some hurdles ?

I sold the other Class C while it was vacant - I saw the writing on the wall so decided to cut my losses. 

On a 2M property you should be able to write off roughly 300-400k, so that would cut your real estate income down for years, but not your W2, because I don't think you would be able to claim RE professional status. 750 hrs and min 50% of your time.

for me I would have been better off donating that 75k to habitat for humans would have got more out of it than a tax write off !!

Someone in the build chain knows the guy who writes the checks.

Short term or long term, everything should function!

Using the search function gave me this, hope it helps https://www.biggerpockets.com/forums/62/topics/1211224-nyc-c...

It is my opinion it is a small percent that do not act with integrity.Do thorough and conservative under writing.  

you can always call or email the tenant in regards to this matter. i personally smoke as well and just would want my tenants happy and not feeling accused as its a big problem with a lot of tenant v landlord situations around the country. you can always say you got a report of the odor of weed and was just verifying the smell with both tenants on the property. you can restate your conditions with smoking. you can always ask if they are legally able to do so as well (meaning medical card). depending on how you want to handle it, if you want to make it a legal warning to the tenant as well, you should write a written letter sent by mail stating you got a report of weed and this is a written warning in case this a problem down the road, you have evidence to show the court if it gets to that matter that this is not your first occurrence. best of luck!

And most were just cure it and buy sub to.. if you have no real equity you have no exit without writing a check.