As a Stessa Pro member, I rely heavily on its features to manage my properties, and while sending over the tax package reports works well (since the Income Statement and Balance Sheet are standard for most accountants), my bigger challenge has been finding a real estate-savvy CPA who doesn’t charge more than my annual cash flow for their services!

The challenge is getting to the house that doesn't look distressed. 

Challenges?

Quote from @Noah Applegate:  This is the challenge buying off market from a wholesaler..

@Rashim Sharma your biggest challenge will actually be finding a lender.There are two banks that have offices in USA and Detroit that often will lend to Canadians buying in the USA.Can refer you to a Tax Attorney here is the US that has hundreds of Canadian clients with US properties:)

Challenges?

I have previously completed a fix-and-flip project, which, despite a few challenges, was successfully sold within 30 days of listing on the MLS.

NIMBY syndrome is perhaps one of the largest challenges any sober house will face. 

@Erica Wilson challenges with LLCs:1) Setting it up correctly.

Not to say buying an existing property doesn't have its own challenges, but development is just different.