You did not mention your current residence city and state.If you are looking to commute frequently or occasionally to NYC, Philly is definitely good option.30th street station is Amtrak stop. you want to be close to that( university city area, south of art museum and rittenhouse).

These prices are not fixed, we occasionally find class A properties for $175,000 but that is unusual. 

There will be small dents created occasionally, as simple wear and tear.

Or ,perhaps , can I rent one rooms to someone or do Air Bnb  occasionally, while still living there?

Welcome to Bigger Pockets Nick, about time you joined :)Good luck with your RE investing career, we should definitely stay in touch along the way.I have a few really good ideas for having a small group of people in the KC area get together occasionally.

There is always the occasional anomaly, but I think that Whitestown and Brownsburg will be easier to find good deals.As far as being "scared to pull the trigger" I would say good for you.

I get auto listings from a few different agents and I usually already know 90% of the house they send me but occasionally a new one slips in I haven't seen yet.

Full disclosure - I did work for him part-time and will occasionally help him with simpler returns when he gets slammed this time of year - but I don’t get compensated or anything, just a genuine recommendation for someone I’ve seen save people tons of money.If you want more info you can message me or just Google LTR Financial Services.

Car prowls happen fairly regularly as reported by people on nextdoor.com, often when stuff left visible, and there are occasional burglaries.   

I will try occasionally but end up putting it on MLS and offering the selling broker their fee..