In terms of the cash flow if I added the additional bedroom downstairs I would be able to Create more cash flow while living here and classify the house as a 4 bedroom which I would assume increase the value of the house.

Homeowners insurance will not work for a STR.A STR is classified as a commercial business so you need commercial STR insurance.There are several different companies that have been mentioned 100's of times.I found Foremost to be the best and least expensive for me.

I have loved using this strategy for my first home and would love to house hack again and use the same model for my 2nd home.However, if I move out of my current house and rent it out my understanding is that I won't be allowed to rent out the top and bottom units separately since it isn't classified as a duplex.

It was deleted and the message I got said it belonged in the classifieds, and that forum doesn't exist.

@Travis EastonPlease post your ads in the Classifieds page https://www.biggerpockets.com/forums/517

I think you are suppose to post in the classifieds.

Redfin has classified the asset as being apart of the "Hillcrest" community and it's positioned right off of 295 and is a 3 minute drive from Capitol Hill.

We would be living in the property for either a bit over a year or only a few months depending on when we decide to begin our program.My question is, when we are getting a mortgage, should we classify this as a primary residence, or should we classify it as an investment property.

I found out that a new guideline for Fannie and Freddie recently went into effect on June 1st of this year requiring complexes to have "entire complex replacement coverage" in their policy or they would not be able to lend on it and it would be classified as a non-warrantable condo. 

If you get further up the shore into Lake County, they recently went to classifying STRs as commercial properties which make things a bit more convoluted.