I also build a drive for dollars list that I slowly add addresses to every month.

I DO NOT care whether he drives a Toyota himself.

And then the last hurdle is that driving miles between your home and your rental properties by default is considered to be like your "commute" to work, and your commute doesn't count as business miles. 

On 1 townhome in MN I spent $17,000 for one reroof, $7500 for a new drive way, and $10,000 for a deck replacement.

I'm betting he'd drive to that area.

A nice portfolio is 10-40 properties, and yes you should drive by your own assets to check for broken windows.

I have a client in Reno doing two reverse 1031 exchanges and we've been able to secure some great deals putting out some cash offers (both weren't even countered). 

Stay away from Philly as their laws are as tricky as NYC's.I would strongly recommend you purchase something within an hours drive from you so you can learn on the job as a landlord. 

Kitchens:-I've been playing around with more expensive quartzite counter tops following the same principle as tile: not a lot of square footage and can really make the kitchen standout.

My favorite C/C+neighborhoods to invest in are Linden, Whitehall, Franklinton, Driving Park, and Eastmoor, to name a few.