Are you in a college town, or what kind of market are you in that so many STR's are sustainable??   

Actually went to college in Ashland.  

I had an idea to rent out the 1st floor unit and give them the basement as well as related living, but without adding an internal staircase.  

I am from the Richmond, VA area - growing up just 30 minutes south, going to college 30 minutes north, and working in and around Richmond for the past 10 years.Yea, you can thank the high paying tech jobs for the high real estate costs in Richmond (Capital One, etc.).  

For instance, the debt shown on the credit report will impact the DTI.Again, what you need is a competent mortgage banker, with no internal overlays and options to portfolio loans in case the conventional loans don't work.

Curious to hear other's thoughts on saving for college through a 529.

You need to make sure you don't miss the college cycle however.

I started looking in troy, and drove by a few but the neighborhood didn't seem to be college students.

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