In addition to the workmanship, you want to work with someone who is good at managing time, people and his relationship with you, his client :-)    We are actually building out a network of approved contractors because one of the biggest pain points investors and landlords face in Philly is finding reliable solutions. 

Get pre-approved for a mortgage, research areas with potential appreciation, and work with a knowledgeable real estate agent.

This was clearly because anyone could do a random search in public records of real estate and do whatever they wanted or guessed. 

Do I need someone who specializes in real estate?

Despite negative cash flow, ROI is not terrible and real estate appreciation is great in this area2.

I'm also a real estate agent here in Los Angeles area. 

There are some very good people on BP who are willing to provide suggestions, recommendations, and insight into various real estate topics. 

@Calum ShallenbergerRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Quote from @Jackson Hartman: I went to the STR Summit in Orlando hosted by the Real Estate Robinsons.

You might want to speak to a real estate tax pro about both of your unique situations tax wise, and the possibility of having a multi-member LLC set up for you.