I'm in the process of trying to raise capital which always seems to be the biggest issue to overcome.

I'd imagine you'd have zoning and legal description issues to overcome..... 

City Housing Dept. has been surprisingly responsive to confirm it’s a legal 2 family home but shying away from answering: what it would take to convert or if we would be able to rent separately as a non-conforming propertyAs a 2 family home, we can get close to expected rental income of 3 family (~$100-$200 less), assuming future tenants would be willing to live on floors 2 and 3 when there are a similarly sized 4-5 bedroom single family homes in the areaOne of the requirements for a 3 family (and I think the main hurdle we’d need to overcome) is the need for 3 off-street parking spaces.

DXE needed to overcome a seller that was very difficult to work with.

@Robert Laird Congrats on overcoming the challenges and creating a successful flip. 

Only if you can overcome all of the possible conditions that would tell you not to do the deal should you proceed.

For most, fear of failure overcomes the opportunity to achieve.

I wanted to let you know of some research on the property I have done and a comp that I found as I tried to find a fair market value for the properties.First, while I want to say that I am still interested in the property, I need to be honest in saying that I'm seeing some problems with the numbers that I am not sure I can overcome to proceed with an offer.

I got my financing options all straightened out, set aside some extra cash, built some good relations with lenders, and really took a lot of steps that involved overcoming fear/hesitation/laziness/frustration.

It's good for overcoming your fears and anxiety (for me it's talking to people I'm not that familiar with).