Like junk bond buyers chasing yield, residential investors chasing out-sized returns occasionally venture into the rental-condo maket - typically lower-income units, since it's an area of the market where owner-occupied demand is so low that you can buy the unit cheap enough to make sense.In my opinion, with older lower-income bills-paid properties you have to practically pay nothing in order to be comfortable with the risks.

Only borrowing about half the appraised value, but should give me an excellent jump start on my next venture!

I have no interest working with them and they are cut loose to broker hop and venture into the weeds of the many mediocre agents that are out there.  

3) Would the financial/psychological/time commitment worth it.4) Knowing what you know from RE, if you were in my position (considering RE as a side venture) what would you do?

My buyers wouldn't even venture through the front door.

Now with higher resolution and apps drilling down on details is easier to put into a work flow of virtual management. 

This is all just my opinion so go for it if you feel it and send me your deals in New York if you would like to do a joint-venture.

Having a flexible job with enough fat to save and invest is arguably a better position to be in for what it sounds like you want to do.If you do work for someone, I would suggest a much smaller venture, where you are able to wear many hats.

Before diving into this kind of venture, understand the market.  

The few times I have gotten off the freeway for gas or a restaurant, I wasn't entirely impressed with what I saw, but again, I never ventured much further than freeway close.If you think you have a deal, you better get a good contractor to go through that house with a keen eye and a sharp pencil while you still have time left on your inspection period.