Second the are going to assume that it will cost them, even if you tell them it is free, and a lot of them have spent hundreds of dollars on app fees.

They will be well worth the money spent.

How many of those would it take to recoup that $20k you spent on training?

I spent a few weeks in Spain and loved it. 

As someone that grew up in NH, knows every corner of the state, has managed both LTRs and STRs across New England, and spent as much time as I can learning from others in different regions across the BP STR forums for years now I would honestly not recommend anyone invest in New England versus areas with far longer rental seasons.  

Did you calculate the value of the time you spent on this?

Congrats on saving up that's an amazing start.I would suggest holding off on flipping if you don't want to do it near you, although with $250k, you probably could find something even in California that you could flip, we hear horror stories from our clients all the time of how they hired a contractor but were not able to watch progress and fly in 2 months later to see almost no work done and most of the money spent.  

And even after going through their video training (which was not worth the $1000 I spent btw, I could have found all the same information for free on here or a number of different places) it seemed really fishy/scammy to me.

I found one after some difficulties and we’ve spent about 20 hours getting my last years books done and this years books done to date.

As a buyers agent, you need to know whatIf we made a list of activities that both agents do along with average industry time spent on each, would that not answer the question?