Here's my situation:My first flip, so little to no experience,  in the eyes of hard money lenders.

What you say are some of the great things to weigh; is the cost of the 1st month's rent worth freeing up my time of screening tenants, doing showings, and anything else involved in the placement process?

Growing up my parents had a few rentals so I had some background, but my involvement mostly consisted of helping to clean, paint, repair, etc. to get the house ready for a new tenant. 

We didn't look at condos recently because of the high fees and risk involved but we do own condos in Wisconsin that do well.

All of the third party providers involved in the transaction have the responsibility of making known any part of the transaction that has been misrepresented once the misrepresentation becomes known to them. 

The Team Leader at the local level will be your best resource for all the details involved with being a part of the Keller family.

Buying the property by myself fyi.B - Not sure, I would like to keep an eye on the property and move out when/hopefully it appreciates to a substantial degree.C - It hasn't been sitting for that long, I've really acquired all of this in the last 16 months.C2 - I will be living in the property and self-managing.. 

I’ve been involved with real estate for quite a bit of time.

As I interview with different brokerages as a potential new Broker / Real Estate Agent, are there any specifics I should keep an eye out for, or demand from, my future brokerage? 

These lines require the involvement of a commercial lender but can make sense.