Any tips on targeted marketing, effective lead generation, or even some "outside-the-box" tactics?

I'll only add when talking to brokers have a "buy box" defined and research commercial deals to understand it as best you can before you have your first meeting or your broker contact will likely consider you to be a low-chance buyer and not take you seriously.

For people who do not mind paying $100 or more a night when they see what fits their buy box, their time is more valuable than searching on airbnb for multiple hours to save $15.

The answer is to value this as any other business generating income, not just stick within the confined box of valuing the real estate only.  

First, I would say bravo thinking outside of the box!

OP look at your buy box, REI strategy and approach. 

start with one piece of land for one single family or a smaller development. or get the buy box of larger developers. why would they need to partner with you when they can do it on their own or find someone more experienced?

Also, try to get two or more electrical boxes so the tenants pay their own as well as heating zones.

If those check the boxes, it's probably the easiest loan you will encounter. 

Not sure where you're planning to take her but here are a few of the local favorites:-Pappas on Taylor Ave (they've opened up a few new locations too)-Kocos Pub on Harford Rd in Lauraville-Faidley's Seafood in Lexington Market-Box Hill Pizzeria in Abingdon (about 45 minutes outside of Baltimore but worth the drive!)