We buy and sell real estate short term and occasionally buy and hold property.

For example we added new siding/windows on one (cost $3500) & they re-assessed us from $28,000 to $68,000 (& we pay $50/$1000).the taxes on our personal residence run over $925 a month & my BIL pays $1200 a month & our home is 2x size, but he admits he has a bloated school system :) & to think you guys had a revolution over a little old Tea tax!!!

I will occasionally post an ad to join my buyer's list or that I buy houses and may get 1 or 2 hits off it.

That is a dam tough job.We occasionally still have arguments about real estate, but not very often, despite buying for 25 years. 

I do occasionally borrow against my 401k for real estate, but again, it was a standard employer plan (back when I had an employer). 

Sure, you'll get the occasional person that has a problem with it but honestly, do you want to work with anyone like that anyway? 

The reason I got my license is to (a.) get referral fees when I come across a seller that I recommend to sell on the market, and (b.) to occasionally represent some of those leads myself to sell their home on the market. 

I dont mins occasional repairs but worried about roofs/foundations

What's NY and Philly got that Pittsburgh (occasionally known as "the Paris of Appalachia") doesn't have?

Repairs, CAPEX, vacancy, the occasional crazy tenant who steals your AC when he moves out.