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 ?

The property was my primary residence for a decade and now functions as rental unit so I am happy with the purchase overall and it has worked out well.

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

And I like the project management function also.  

Keep in mind that I am selling them as affordable fixer uppers and usually only address any health, safety, and functionality issues.

If we bite off people’s heads when they admit disaster, it suppresses legitimate issues with these techniques.Just for context there is a lot of history with the OP and some of us on here going back years (like the thread I linked to above from about a year ago and several others if you use the search function with his name) with him minimizing the risks of how he was structuring these transactions and some of us being cautionary, warning him that exactly what happened here could happen, which made him defensive and dismissive. 

With real estate, you have to make sure each property is functioning at full capacity or you’ll be losing money.You can analyze properties and be pretty sure (as long as you don't rationalize bad deals into good ones) what your numbers will be. 

Just curious... what’s your ultimate goal for that office space..are you looking to boost resale value, or is it more about having a functional retreat above the garage?

@Michael BertschAs a general rule, we only leave a fireplace functional unless it has a sealed, externally vented, gas insert ... and, even then we may disconnect it.Check with your insurance provider and see how unhappy a functional fireplace in a rental makes them.

I never imagined this pursuit would bring me down such a path, and I do not know how well I would function if I had to actually use my pistol.