I think his work is somewhat seasonal so he has some money available and basically just wants to avoid blowing it.

I found 2 available for 100k.

Cash-flow, though possible, is generally not something you'd benefit from here (unless you do it via illegal vacation rental).That said, I would definitely buy a small condo (studio or 1-bed) for myself here, as I'd rather pay myself rather than a landlord, and IF you feel confident enough in doing out-of-state investing, leverage your remaining funds to purchase 1-2 properties that cash-flow elsewhere.If instead you'd rather keep it local, I'd use your available funds to purchase 2 condos, one for yourself and one as an investment.

Even if you don't offer or its not available long, you'll need the approval for any property.

Also, amount of available rentals on the market seems dense.

We haven't however discussed costs for me to work with my local real estate agent to identify and do the pre-purchase due diligence on the properties as she most likely will not be available in person to see them.

I feel confident in my ability to find deals with the resources I have available to me and my marketing background.However, I realize a lot of investors don’t have that and have other ways of doing so.

I prefer to be proactive in this regard, and I use an LOC to have the cash available if/when needed...if I haven't sold  the property before I get hit.Proactive for me means I cover the following costs:1 - Roof - When I buy...if it looks like it will need replacing within a few years. 

In Ohio, divorce decrees are public record but only available upon request. 

I am having difficulty with getting available time with each currently occupying tenant to change locks, get leases signed and everything else.