Given this was our first time purchasing an investment property, working with a partner on a cash deal, and understanding how to get FSBO deal completed, we had to learn a ton and ran into multiple challenges.

Listing on multiple platforms does affect ranking by platforms but not as much as you think.  

House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

I recommend talking with an experienced broker who can help you shop multiple lenders  

With the right PM (I always recommend connecting with multiple who specialize in the types of properties you're buying), they should be able to help you stabilize the property and hopefully keep the tenants for multiple years. 

I have multiple condos listed for sale in Costa Rica.

Not all VA loans are owner-occupied as the VA gives you an allotment so you can have multiple properties with VA loans depending on what they clear you for.

I've seen banks be very competitive with blanket loans that cover multiple properties and/or multi-family properties, e.g. 5+ units.Mortgage Brokers (obviously I'm biased) - Brokers have the ability to work with all of the above and can get you to the best lender for your scenario right away instead of having you waste your time with the wrong type of lender.

Even with a great opportunity, trust is the foundation of any partnership.In my partnership, we had already worked together on multiple deals—me as the agent and him as the investor buyer—so we had established a strong foundation of trust.

We love thinking outside of the box to be a creative investor using multiple strategies to achieve multiple streams of income & financial independence.