You will be competing with people who have 'boots on the ground' and can visit any property owner with short notice.While wholesaling from afar is possible, it is recommended to begin closer to home.

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 only thing that I can think of is that the rent price could possibly be too high. 

Just trying to get as much information as possible since this will be a huge leap for us into this type of investment. 

That would allow you to put down less knowing you have that income coming in.Otherwise, is it possible to consider moving somewhere more affordable so you can reach that financial freedom you want? 

Each connection, no matter where they were based, provided valuable insights and support that made investing in distant markets possible.

Would that be possible in my scenario?

Your value is, to provide sellers that don't want to list, with a way to get cash for their house and provide buyers with discounted off-market properties they can buy to make a profit on.I am not saying it is not possible to wholesale from the MLS, but it seriously defeats the purpose.Focus on becoming the person/company that offers the most and best value and you will succeed.

Jeff,I'm new to property renting.Would it be possible to get a copy of the excel sheet you created?

You may be profitable, but I'd prefer to avoid the possibility of having to do unnecessary repairs or not holding my tenants accountable for damage when I know their actions might have caused any unforeseen damage.