@Caleb Rehg depends on the neighborhood!

Not as many complexities with a few rentals, but there can still be significant issues depending on entity structure - even if they are all "disregarded" entities for federal tax purposes.If your W-2 is your full time gig, and they are all passive long term rentals, there very well could be likely not a lot of active planning to do on the real estate side, outside of getting some general knowledge out there, having some longer term plans, and ensure deductions are being maximized in the isolation of those 5 rentals.

This will vary based on the owners specific situation and tax regulations in your area.

Obviously dependent on how much you made in the most recent year, but you never know!

Typical rates are 8-12% of income either monthly or yearly depending on manager.

Depending on you budget you may want to consider outside of downtown.

It depends. 

Cold outreach: direct mail, cold email, cold texting, cold callingGet a list, scrub list to get contact into (depending on how you will communicate), reach out, follow-up to the 99/100 owners that aren't interested every few monthsCold calling will have highest conversion but lowest volume.

Whether it's better for you to sell your home or not really depends on your goals.

I think it will depend on your area as most of these third-party companies pull the data directly from the county and may or may not filter that data well to pull out vacant land.