You have hit the JACKPOT of resources for real estate investors.

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

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

Do I need someone who specializes in real estate?

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

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

@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.

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

As primarily a luxury STR buyer's broker and 20 year mortgage broker I can testify the importance of a reliable and experienced strategic mortgage partner. 
So what is an integrated mortgage partner? 
- A licensed N...

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.