Ensure that the savings from the new loan outweigh the costs of the prepayment penalty and any closing costs involved in the refinance.6.

Because first and foremost it requires you getting INVOLVED, putting in some rep's, and if you won't get involved and won't put in the rep's you will never, I repeat you will NEVER succeed in investment real estate or any business venture EVER, full-stop. 

I assume there’s no realtor involved or they’d be upside down.

I suspect this would happen if various parties were given the ability to ask questions in nearly every application for what this thread touches on - and I have major concerns about integrity (and credibility) issues involved in putting yourself in a position to defend this position if ever challenged. 

I won't ever close on another OOS property without walking it first but that involves paying for lots of flights and hotel/rental car costs if flying out there to make an offers but the $1500 to $3000 would be worth the cost to me to save on future headaches. 

Short-term rentals (STRs) offer a way around these limitations by being considered active income if you meet certain material participation requirements, such as working more than 500 hours or 100 hours, surpassing anyone else involved.

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. 

Just bear in mind that trips to Maui involve 'discretionary' funds...A few more things to think about during your due diligence. 1.

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.

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.?