You will run into this occasionally.

I’m looking for mainly to buy and hold and maybe an occasional flip to help fund my purchases of rental property’s.

I go to Rochester occasionally.

This could be as simple as meeting up for coffee occasionally to discuss deals.

That sort of thing has me thinking that the line between hotel and vacation rental will be blurred to the point where governments force vacation rental owners to abide by hotel rules and taxes.

These days, I'm a little bit more strapped for time with my business so I'll occasionally make the general meeting (or send someone from our staff in my place) but I usually switch off between the Chester County subgroup, the Montgomery County subgroup, and sometimes the Delco subgroup.

Generally speaking, these types of deductions are going to be added to depreciable basis, but they can occasionally be at least partially deductible, depending on what you've got going on.Consulting with a knowledgeable tax pro will get you a more definitive answer. 

When I look at Airbnb there don't really seem to be many "dedicated Short Term Rentals", it moreso seems like homes that people just have up for rent occasionally. 

I have lunch with them occasionally and I always ask them if they can both quit their jobs and retire after five years of investing in multi-family apartments with lifestyles.  

I live in Ithaca, NY and I run into that problem occasionally with people looking to buy short term rentals.