My outside pursuits include tennis, golf, hiking, road racing, and dancing.

In 10 years, in theory I should be making more money from the Day Job so I should be able to swing the principal+interest payments.

Starting to look for #2 in 2018, also in Philly, likely another owner occupied, possibly flip via FHA 203k if I can swing it.

But I'm guessing closing costs on the new property are going to be close to 10 or $15,000.  15,000 to sell my property and $15,000 to buy a property is a swing of close to $30,000 in costs having nothing to do with the purchase price or down payment.

have often contemplated RE investing as side career (rehab - love love love fixing up my house and swinging a hammer!)  

I currently work in the golf industry as a PGA pro and focus on tournament sales and marketing.  

Pay an agent to swing by house to check on it. 

If you can swing financing with 20% down, you get about a 54% return on your money after figuring 10% for capex, 10% management fee, 8% vacancy, taxes, and insurance.

I'd like to be around her contractor, swing a hammer, pick people's brains, see how they work on a daily basis.

I'll add this to my routine as I make it - in fact I've done it on all past properties, just getting to the swing of a routine!