Complicated usually means expense.

We want to fight this expense because we aren’t backing out just cause, we are backing out for a serious reason.

So is the average homeowner so it can mean less competition and more money.

Premier properties are excelling and doing better than expected, average properties are suffering massively.

If I do end up purchasing a duplex for 299k, I would be living in one for about a year and rent out the other at 1300/month, In which I would still be paying out of pocket for the mortgage (est. 2122/month as per zillow) not including the other expense.

Sure, what you do will affect those latter two, but nothing about the realtor.Perhaps with in your setup the lawyer and accountant may need to confer, but the accountant will prepare the return according to whatever income/expenses you provide and whatever legal structure your lawyer puts together for you. 

Both programs are pretty expensive.

Average Houses are around 600k where I am living which means if I put 20% down I’ll be looking at a payment around 4500$.

Buyers today are still looking for good investments (obviously), but the most achievable scenario is short-term renting a property to help subsidize (or fully cover) expenses while living out a lifelong dream to own property in Provincetown.

Even if she leaves and you lose some rent to vacancy, you will more than make it up if your average tenant stays 2+ years as they should be.