Used to see him and his ads all over.

Their ads sounded like it was an education session with a meet and greet -- no sales pitches.  

I added a pool and did some landscaping and have been using it as a family winter retreat and renting it to a STR operator the rest of the year.

There are a few markets in the US where you are forced to look outside like LA, SF, NYC, Boston etc, but even for Chicago investors it does not make sense to invest in Milwaukee due to the added cost and complexity

You are correct that it can be called but you are also usually given the option on either adding to the account or selecting what to sell.  

Realistically if you have around $18,000-$22,000 liquid per house and its at least drawing even you eliminate the vast majority of issues people run into with over leveraging.

Thus, you will have a higher profit margin.You will have added closing and holding costs when paying with Hard Money.

Adding a couple of clean outs on new pipe should be no big deal. 

Can you eliminate markets that wont work? 

Adding value to a property and then either selling or refinancing to pull your capital out is a solid way to build momentum, especially if you're okay breaking even on rental income.