I've listened to enough podcasts to KNOW that I have to build the team first before EVEN putting a contract on a property.

Particulars:1) 1st SFH rental property cash flows $400 and we have a 2 year lease agreement that ends in 2025. 2) 2nd SFH I currently live in, I would rent out and probably experience a negative cash flow of --$100 cash flow for first year, break even 2nd year, and build little cash flow moving forward.

Perhaps even just own the real estate under your own name while you are getting started and get a good insurance policy on the property. 

Make sure you're performing credit checks, background checks, verifying income (calling employers and even checking bank statement if you need to), and calling former landlords to inquire about/confirm their habits as a tenant (cleanliness, respect for neighbors, paying rent on time, etc.).If you don't think you're capable of this, definitely find a good property manager!

I don't even know where to begin with this.

Spend an outsized amount of time learning how to do it, even if you believe right now that a third-party property manager is the way to go for you.

If the price is right, it is even  a deal to redo a complete raised foundation.

Even in high traffic cities it can be tricky to keep occupancy over 85%, so you would have to be very competitive with your property to hit the 60% mark in my opinion where seasonality is so strong. 

They have nothing directly to do with eachother, even if they were across the street from each other. 

Thankfully I bought them dirt cheap after the '08 meltdown so after years of break even I made money when I sold them.