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 ?

Quote from @Lionel Quiambao:  ... and maybe throw in the option for the tenant for more speed at an increased rent to cover the additional payment. 

This means you'll want to "write off" expenses related to a property you have in service because if those expenses don't benefit you this year they could in the future once you sell the property.We can get into a lot more details with the "if" "and" or "buts" BUT I think this would be the "simplest" answer without diving into your specific situation here.I hope this helps! 

That feature is bundled in a Resident Benefits Package I have as an addon through Second Nature. 

Additionally, in the R-7 and R-8 Zoning Districts, you need a Conditional Use Ordinance from the City Council to authorize the conversion.

What do you think franchise would be still better or starting from scratch ( long term benefits).

I want to refurbish the entire house, including a complete kitchen and baths renovation, add an addition on the east side, new roof and siding, new flooring everywhere, paint inside and out"Then ask the GC to go over and put this into a more formal document.

In addition, committing ~ $200K requires some level of sophistication on the part of the investor and you are more likely to find someone to agree to your terms in smaller transaction sizes, but even that will be difficult. 

(cash flow, tax benefits, potential for appreciation) Whats the timeline?  

The third, I think I will break even or small profit, but it will be on the longer end of the hold, like 7+ yrs overall.I have not had any additional capital calls.