By buying a fixer upper I am able to be all in after repairs for a lower price and I know the systems will be updated and pretty reliable.

Very difficult area to work in and have issues finding reliable managers and contractors. 

Also, did you find any reliable agent/contractor to look for properties and carryout rehabs?

I'm looking for a team who can paint as well as fix issues like broken steps or cabinet doors.Has anyone in the forums that operates in the norfolk va area worked with someone who is reliable and can recommend someone?

First, does anyone know a reliable handyman who can replace a couple wood siding pieces?

Say your income is still not reliable.  

On the other hand you’ll have a reliable tenant in dad, property taxes are low, insurance is low, and you can probably make a tax deductible trip to visit dad each year (confirm that with your tax person).

I would need a trusted RE agent, to learn how to properly evaluate a potential property, how to quickly analyze repair costs, find a reliable handyman/contractor, analyze if I need to use a PM or to self manage and all that is entailed with that, learn to fully maximize rent, and the list goes on.This just seems like a steep price of time and effort to get into a market that can be volatile at times.

I had a couple of different people cut the grass before I found a reliable lawn service and I paid those guys cash.

I realize now I need to balance best pricing with reliable quality work along with strategic payment plan.