This is really a better question for your accountant first because it depends on what you are trying to offset.

With $50K—$100K, you could fund a rehab and refinance to free up most of your equity for the next deal.Cons: BRRRR often requires more hands-on involvement, especially managing contractors and timelines, which could be challenging with your demanding job and family obligations.

And treat this as 1/5th space as a rental.Or down the road, would it be better to have the entire property (home & garage/room) rented out to everyone involved and the property become an investment property. 

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.

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.? 

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.