You still haven't defined what you consider to be a "crazy amount"?

Its a buzz word, as opposed to a clearly defined strategy...

I think a lot of people go into business either with a specific idea or with a hobby, not realizing that's one of the least important aspects of running a business.

Some people like to know there are tenants in already so that they don't have to worry about that aspect.

I love the diversification aspect, as we have invested in large commercial multi-family, trailer parks, hotels and even a steel manufacturing plant.

They spent years in corporate America learning the business.If success is defined as raising as much capital as possible, quickly, you need to be a marketer first. 

You have to become the guy how is known for knowing deals.I don't think mailers are a complete waste of time, especially if you have a defined audience, but I built my following online, particularly with a YouTube channel talking about Milwaukee Real Estate.

Then you can define your buy box and start searching with an experienced investor-friendly agent.

I have time to handle all of the guest bookings and management / scheduling of cleanings and maintenance, but I don't have time to do all of the messaging that is required to maintain good communications with the guests.Anyone have experience with using VA's in the Philippines for handling guest messaging aspect of STR's?

If you can run a flip from out of state you can defined run a STR remotely with the tools Vrbo and Airbnb provide.