I would narrow down my choices based on specific set criteria, then take a trip (week end trip) to places I would like to invest, meet with brokers, agents, property managers ... etc.

Once you do your first deal it will be so much easier for the second one.  

You still have several options, depending on if you want to invest directly in individual properties or be a bit more removed:Full-service turnkey investment: Should be mostly passive after you do your due diligence and pick a provider, but don't skimp on your homeworkYou choose which props to purchase, but have no control over tenanting choices, some say in large maintenance expensesAvg cost for solid B/B+ prop in Birmingham (and some other markets but this is the one I have data for, since it's my market) is about $100k per door; you'll pay market price for a tenant-ready, fully rehabbed propertyPartnering with someone who does the on-the-ground stuff while you provide capitalCan be passive if your partner really knows their stuff, but more likely you'd be fairly involved with the choices madeMore control since you call the shots with your partnerYou can pick which markets and price points you're interested inPotential for higher returns (ie buying distressed and then forcing equity through renovation) if your partner is experienced and can execute consistentlyInvesting in a syndicateMany investors pool funds to invest in much bigger projects like commercial space or large MFRs, or in larger portfoliosVery passive, investors are not responsible for project vetting or management, but you have no controlMay have higher bar for entry, some syndicates require large investments and you'll need to have liquid cash on handBuying shares in a REITLike an ETF but comprised of real estate investmentsVery passive, but no control over which assets are held in the fundHighly liquid, easy to buy and trade, lower bar for entryEverything is a trade-off between passivity and control, time and money.

Zoned business and residential.Your choice to make this your beautiful new two bedroom home, office, or combination. 6 Meetinghouse a great place to call home.

It makes a life a little bit easier on whoever is doing the title work in the future. 

Maybe someone will act on it and buy, This kind of activity keeps the price up and makes it easier for local investors to sell to OOS entities. 

Is there some simple math that would make our decision easier?

But the more assets you have the easier it is to get one.  

They have a choice of buying the home, or moving out and letting the next guy in line buy it.You offer a program to buyers with a couple grand down and affordable payments for 3-5 years on the balance.

But it's still a choice that you are making for a bad act that wasn't even committed by the tenant.