Why type of price point are you looking, what anticipated ROI/cash flow, how much time do you want to be involved in, what is your risk threshold, how long do you plan to hold the property, are you looking to invest locally or open to exploring other markets, etc.? 

TIAI personally don't like the receipt scanning apps because I think they are overkill and they only account for half the record keeping you need to do.

Getting multiple contractors involved will be your best bet to get a reliable estimate, though you need to come up with a scope of work.

It involves investing in strong growth markets, diversifying, and buying distressed properties.

We would meet once a month and just hold each other accountable for the steps we are all taking in building our RE business. 

There are lots more that require a little bit of human interaction and a few more that need full involvement of a person - answering the phone, some AR and AP.

But with this being a 5 unit multi-family building most lenders do not offer a loan product that will take the STR revenue into account. 

Like most things in real estate, a lot depends on the circumstances of the individuals involved and not just the numbers and figures.I hope this helps explain my thoughts, and I apologize for the lack of clarity when I defined "arbitrage".

The best strategy depends on your goals, but here’s a breakdown:Selling outright would result in paying capital gains tax and depreciation recapture, but since the appreciation is minimal, the tax impact may be relatively low.Gifting the property to your son could potentially allow him to sell it with a lower tax rate, but since he hasn't used it as a primary residence, he won’t qualify for the exclusion of capital gains tax on a primary residence, and you'd need to account for gift tax implications.1031 exchange could defer taxes, but you would need to purchase a like-kind property of equal or greater value and meet all the IRS requirements.

@Edward SegaarBigger Pockets is a great place to find a real estate accountant.