I am actively looking to expand throughout the Caribbean. 

Most likely yes.)As a buyer I might say something like these 4 major items add up to $3,500.

Keep in mind a few things - many major markets currently have a glut of multifamily projects so you may be competing with large apartment complexes with amenities offering incentives in a competitive market. 

What are some pros that I can highlight from the seller’s perspective.Here are a few that I’ve come up with:1) monthly income at a higher interest rate;2) avoiding a larger tax bill by reducing the purchase price (on paper);3) a promissory note that they could potentially sell down the road.Any other major ones I am missing?

@Andres Felipe Alba Hernandez Yes, neighborhood covenants can sometimes restrict certain activities, including short-term rentals (STRs) or renting out parts of a home, even in areas without a Homeowners Association (HOA).

But we have a smaller one (1100 sq ft) in a lesser subdivision and not gatlinburg  that is getting tons of activity since we put it up for sale and it isn't complete. 

The vast majority of lawsuits against landlords involve wrongful eviction, security deposit disputes, and Fair Housing Violations.

Greenfield is a growing area, and being in a golf course neighborhood across two lots adds a ton of value to your options.I’d recommend starting by connecting with local investor groups or meetups in Indianapolis—Facebook groups or here on BiggerPockets are solid places to find people actively working in that market.

Is their current portfolio distressed, or was the majority of their current portfolio purchased at the peak of the market, indicating that they might be in distress in the near future. 

We buy houses in major markets in the states of TN, TX, OK and AR.