@James Zobrisky Relying on cash flow to fund future acquisitions is a challenging proposition.

When analyzing properties, it's helpful to run a rental stress test to see if the deal can withstand unexpected challenges.

Good Lord, given what he’s accomplished with his challenges (not just Quest, but also being a very good man), what in the heck is our excuse for doing less?

Investment properties prove to be more challenging, but not impossible when titled in your own name.  

@Philip Beckwith typically in Michigan, you can only do a tax appeal in February.The instructions will be on the back of your winter tax bill.You will need to have great comparables to challenge the City Assessor's valuation.

However, in my experience, those who rely exclusively on this strategy can face significant challenges.

Managing a property hours away can be challenging if any issues arise, but having a third-party property management company could help handle those situations and make things more manageable.I think you are in the right place to gain some insight on what would make you successful. 

Your approach here has definitely given me a lot to think about in terms of spotting hidden value.Curious, with the deferred maintenance challenges you faced, was there anything unexpected that came up during the rehab that you’d approach differently next time?

Challenges?

Technically you are going to be able to claim the interest, since you are the one that's going to receive the 1098-int, but what's likely to happen is that the buyer is also going to ask for/claim that interest and then you are both going to be in a jam with the IRS.