As mentioned your biggest challenge is going to be selling the package at/close to same time. 

One of the biggest pitfalls is the age of the buildings I'm looking at. 

I recently completed a major renovation on my property financed through a Fannie Mae HomeStyle Renovation loan, and I'm now looking into options for removing Private Mortgage Insurance (PMI).

I feel like every project has its curveballs, and sometimes it’s the unexpected stuff that teaches us the most. Maybe it was a hidden issue that turned into a big project, or a small upgrade that made all the differen...

He's still very much in contact and reachable, but my biggest fear is that he will run or file some sort of Bankruptcy.

Have you looked into becoming a private money lender to put your money to work while you wait for your next purchase?

The biggest downsides are that they usually have higher rates and require larger down payments.

You can send me a private message for more info

The biggest thing I have encountered in numerous inspections is chipped or flaking paint in pre-1978 homes that have children living in them.

Good question, I think the biggest question will just be your overall timeframe and how quickly you want to get everything done.