We started with flipping to build enough cash to start buying income producing properties and have decided STR's is the way we want to go.

Quote from @Bocondo Williams: That's the problem with free software: they eventually have to generate revenue, then they want to produce profit, then they want bigger profit.I think most software is going to charge $1 or more for every ACH payment.

This means cash flow is producing 4.3% ROE.  

Another concern I would have is that if we enter into an economic situation where tourism declines and foreigners stop buying expensive second homes there, you could get stuck with a property you can’t sell that isn’t producing much income. 

He has also invested like this with us on a couple of high-producing STR beach houses (that net each of us around 70K per house each year).

Because I invest in income producing property, my net rental yield is around 8%, with yearly increases, leveraged with 4-5% loans, creating a net cash flow and debt reduction yield of about 10%. 

I echo what others are saying on here that hiring someone from fiverr or upwork tends to not produce great results long term.

Flipping is a side job and won’t produce steady mailbox money for life while you vacation and nap.

We also get calls from good, professional agents that are almost apologetic about their offer where a newbie listed to a podcast produced by some joker that doesn't really know what they are doing themselves.

I've helped manage 100s of estimates for residential contractors, producing nearly 100 myself.Disclaimers: I'm not currently a contractor, nor appraiser, nor licensed.