Are my concerns legitimate or overblown?  

If the listing agent is also giving you the "projected rents" I have unfortunately noticed some legitimate inflation in those estimates.

I'm just curious on how others have found legitimate contractors in their cities. 

I am only wholesaling to get to the point where I can buy the deals legitimately and flip them, rehab and flip them, rehab and rent them, etc. 

We have become swamped with leads and have turned 100% towards disposition now and finding legitimate buyers.

Look for a legitimate REI group in your area.

From my experience, any legitimate contractor I've come across would not want to spend their time looking at a potential house I'm interested in buying, since the probability I will actually hire them to do work on that particular home is very small.

The good news there are some legitimate management companies who are not out to rip you off.  

It's a bit early for me to start legitimately shopping around, but eventually I want to purchase a small multifamily and house hack it.

However, if I advertise and rent it out as a 1br, will the tenant have the option to move in and then say it's not a 1br and then legitimately not pay rent?