I was in the same situation and I started doing the research in February of 2021 and after a few declined offers, I purchased my first home as a house hack in September of 2021.

I purchased my own STR 6 months ago and have been seeing and reading about the same trends in terms of declining bookings.

As long as you do not accept the reservation (decline the reservation), there is no problem. 

Several school districts have had MAJOR incidents of facility misconduct (google it, I don't want to get into specifics) and both purchasing and price value have declined and not yet fully recovered.

Those that grossly overpaid within the last 12 months and are in markets that have since started to decline are making up the majority of those that are upside down. 

Without a sale in past three months that are lower than what you paid you need to wait until you have the evidence.Philadelphia market has declined about two percent in past sixty days.

I'm curious to get your feedback on areas that seem to provide good cash flow like Rochester, NY and Cleveland, OH.  1) Is the general thought that these areas might not make the best investments for a buy and hold investor given declining populations and a potentially low likelihood of appreciation?  

I do it on every property.Pro is you get tons of added write-off $$ on a declining basis. 

What role would you expect declining rents will play on the median price of houses ?

The rental pool selection has declined over the years since inventory is so great for rentals.I am referring to a class a rental property.Would you rent to someone that had an eviction Filing 10 to 15 years ago?