Flat rate of $800/month to a bookkeeper that specializes in real estate.

@Michael MattinglyRecommend 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.

If your wife is a stay-at-home mom and is involve with managing the rentals you may want to explore Real Estate Professional Status as an alternative tax strategy or along side your STR tax strategy.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I called a local real estate attorney and he advised against it.

I live in Missouri, and am looking to dabble in real estate. 

Income received prior to that date would be considered rental income.Here's a good article on the facts and circumstances that would need to be considered: https://www.jmco.com/articles/real-estate/lease-options-sale...How it is ultimately treated will affect both the buyer and seller.

Business or Real Estate?

I'm Bella from So/Cal, passionate about Wholesaling Real Estate. 

In general, it is a tough RE market but house hacking is perhaps the best not real active option.