One strategy you can use is to continue what you are doing and house hack and rent to traveling professionals. 

I have the knowledge and skills for contractor work as I have been doing handyman work for the past 10 years, as well as learning the roofing trade with a professional company.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

One housing authority wouldn’t even entertain the request, while another was open to it because it was an affordable housing property, requiring just an application for the exemption.From my experience, dealing with government agencies, especially when trying to save money or get financial benefits, can be a slow process.

My goals are to start building an investment portfolio of professionally managed (I could tell you all the reasons I will not do it myself) multi-family properties and, in time, develop a property in the Northwoods (Wisconsin/UP).

My application includes an acknowledgment that everything is true and complete.

They will get the highest price and the best terms for their property by marketing it professionally and exposing it to the maximum number of retail buyers, which means putting it on the MLS with an agent.

I would first check city/county STR rules and HOA (if applicable). 

Here is a newly created resource on BiggerPockets, which touches out cost segregation, accelerated depreciation, bonus depreciation, depreciation recapture, Real Estate Professional Status (REPS), STR Loophole / STR Strategy, example properties, and more. 

•If your goal is stable long-term tenants, you may want to target young professionals or grad students who stay year-round.4.