Happy to connect with Boston people.

Just curious why people think they should be in jail?

My neighbor has listed his but also has had occupancy issues as an STR and said that most people looking for either rooms or cheap stays but I can't comment on that as I have no experience listing as an MTR.

My question is how do most people make the jump to the 2nd STR property if you're generating $25k per year on the high end? 

People are losing money.

My question is what have people used with success to best track their time/investments over the year?

You can just have people rebook if they want.We bought our lake house for use to use on occasion as well.

I would love to meet and network to people in South Florida , and find a mentor or someone who has taken a similar investment route that I am doing from flipping to owning rental properties.Really just meet likeminded people. 

People buy a house because the house fits their needs, financing is icing on the cake.

The people who struggle here usually underestimate those factors.One thing I do differently than most: I share actual performance data from my rentals—purchase prices, rehab details, rent numbers, lessons learned, and backstories.