Like you said, I want to seed different strategies I can implement with the limited capital I have.  

Booking.com fidnt blink at my decline now 3 weeks later, they tried to cancel again claiming their dates change and they couldn't make it.

However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

You don't know for sure exactly what their occupancy rates are but you can certainly get a feel for it by seeing what future dates are open.

The appeal of student housing to rental investors lies in its ability to provide a steady income stream, especially in areas with high enrollment growth and limited new construction.Given your experience and the quality of your properties, you should find a receptive market among rental investors.

Very in-depth and up to date. 

They view each loan individually and have been lending to me even though I only work my W-2 on a limited part time basis.

Do everything right: To include but not limited to pro photos, professional quality design, durable furnishings.  

If you have a credit card with a high limit or a line of credit on the existing duplex that might give you some wiggle room.

An investor is going to want to have a specific date they can get their money out of the deal.