I've been wanting to get some advice from people about my specific situation, but there's a lot so I'll try to keep it to the point;In short, I'm wanting to "officially" start my real estate investing journey, making it my source of income - and I'm wanting to do house flipping as my strategy, at least initially.  

Short, sweet and right on the mark.

Managing a short-term rental (STR) can feel like a full-time job.

•What types of properties do you usually focus on—short-term or long-term rentals?

Take short-term rentals - they do provide several tax benefits, but they are hard to run and very hard to succeed at so people make the mistake of choosing the tax vehicle, get the benefit, and then lose money on the investment and hate it.

in a few short years 1 property has produced over a $1/2 million in equity, thousands in cash flow, was leverage to buy another property which does the same and leverage to buy a small cash flowing business. 

There are some great tax strategies for short-term rentals, but very important to be aware of the personal use rules to make sure 280(A) doesn't become an issue. 

Here are some ideas to make raw land pay for itself:RV or Tiny Home Rentals: Set up RV hookups or tiny homes for short-term rentals.

The short answer is, yes, you can absolutely buy a trailer on private land and rent it out to Section 8 tenants. 

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