You can get the STR data from something like AirDNA and then check out what your competitors offer on sites like Airbnb/VRBO.Negotiations will also depend on their cash flow and how much of the business you buy.

I am a building contract of decades, I have trained inspect dept's, journey in 3 trades, and over $200m in flips under the belt, mostly to pre '78' homes. 

Years ago I attended a training class.

I would add this: the best in their fields train all day/every day.

To put it into terms; I was asked to come a chair a agent training at a big-brand brokerage (KW) which was about REI.

They have a lot of training available for things like prompts, activities, tracking for renewals, etc.

If I'm not onsite, I really rely on hearing "hey, consider replacing this carpet".

I do have an onsite manager that collects rents and shows the units for discounted rent.

If you are going to expand your market or consider bigger properties, I suggest you investigate some multi-family training programs like that offered by @Gino Barbaro. 

Also experienced GP’s don’t have the time to “train” someone who is not a long term solution.