To add to @Ashish Acharya, I would recommend using your retirement funds for notes that earn a nice interest rate, if you're into self directing.Given that you want to purchase a short term rental, I'd highly recommend not doing this within an IRA/401k. 

We identified it on the MLS with it's low asking price and nice aesthetics.

I think keeping it simple but nice is best.

Philly is a nice option, but you have to study the blocks for about a year to be sure you understand the area you are investing in.

I would have to assume that if they've had it that long, they could absolutely have some really nice cash flow going.

my hope is to get a nice unit for my son at below 50% of retail.  

They're charging second mortgage rates on a first mortgage, nice investment if you can get it.Getting the former owner to sign a second mortgage for the amount you paid at tax sale works, if he pays, and if he signs. 

A scenario like that would likely result in getting your entire investment back upon refi and also a nice cash-flowing rental to manage.   

Nice job!  

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