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.

(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. 

Even though they cover all the costs, you'll still have to pay for closing expenses, about 3-5% of the loan amount.These loans are better for people who know their way around real estate, not so much for first-time buyers or those new to this game.Talk to a money expert, check out different lenders before you decide, understand all the risks, and look into other options like FHA or VA loans—they might be a better fit, depending on your situation.

I think a walk in shower would look much better, but obviously it would be a lot more expensive and it’s the only shower/ tub in the house so I’m not sure if tenants would want or need a tub in the house (especially if they have little kids).