The properties that I liked I could not afford, and the properties that I could afford I didn't like.

Seems that properties are relatively affordable and one of my friends bought his first investment property out there. 

If he has to do all that he is going to be resentful unless you are taking on other tasks of similar You should look into off market deals, tax sales, fsbos, and some on market properties. 

The properties with poor initial cash flow often have good/great historical appreciation.

While I may not build the underwriting models from scratch anymore, I still take a close look at them to provide valuable insights and make informed decisions.Apart from underwriting, I also have a strong passion for property management and renovations.

In this case, if we use 75% LTV there is $20k plus refi closing costs trapped in the property.   

@Gregory MoserHow much do you know about Property Classes?

The house is solid structurally and in a great area that I expect to appreciate, but I need to replace plumbing, electrical, add a bathroom, and paint the entire house inside and outside. 

As far as finding a new property manager, I always prefer to meet people in person, but if you are far away, you should be able to vet property management companies from afar.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.