Will a new vent out the side wall be needed for venting add another $200.00 or so.Tankless: Very expensive but worth it in your own home.

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. 

I typically export the monthly metrics from my PMS, then use a excel work sheet to break down gross, fees, expenses for owners on their end of month reports. 

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.

Both programs are pretty expensive.

(You will need to declare the income you receive but can also write off any expenses and depreciation like normal.)What kind of tax benefits would we get as rental property owners.

Both are different, one gets less money but less time/hospitality/upfront costs; another gets more money, with more effort, more hospitality, being more available for guests upfront, plus extra expenses on the front end. 

Complicated usually means expense.

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.

My expenses YTD in this market are currently 44% of revenue YTD.