However, I started using Hostaway as the PMS, which requires a Stripe account.

If it is follow the requirements in the documents.

It's possible the deceased father agreed to let her manage the property and keep the rent net for her troubles, but the title/ownership remains in him so his heirs would inherit it as a legacy.I suggest your friend familiarize himself with the statute of frauds which I believe requires agreements regarding real estate be in writing to be enforceable.

All the cruises we really wanted were completely sold out except on less desirable cruise lines (the motel 6 of the Cruise lines). 

@Yanting Wang many investors are buying, "build to rent" properties.They are all being told that in buying a new construction property, they shouldn't have maintenance issues for 5-10 years, which will increase their cashflow/profit.Well, tenants have a way of breaking things, not taking care of problems and letting them become maintenance issues, and this is on top of the fact that most new construction properties require several warranty repairs by the builder in the first 12 months.As others have pointed out, you must live in the property for the first 12 months for an FHA mortgage or take your chances with committing mortgage fraud.

What is the process that requires me to be licensed with FINRA.

They require a lot more hands on care and this could put extra stress on you if you are not local.

take a higher percentage downpayment make sure they are liquid, sign a longer term lease, give yourself out clauses, ask about ada accessibility or requirements for occupancy from the VA 

.* Go to nearby market areas/neighborhoods and find reasonably similar duplex sales and adjust for market area/neighborhood differences as required - along with the other adjustments.* Find reasonable 3 or 4 unit (not more than 4, and they can use sfr's, but those are typically not as good for comparison.

I require no less than 3 profitable exit strategies, if I can't hit that mark it's a no-go.