I do have folks that don't book because of that.That is a good thing as not understanding the distance to get places will create bad blood and cause those 2 and 3 star reviews which no one wants to see.Like @John Underwood, our place isn't cheap so we don't get the folks that destroy places.The bottom line is that you are renting out an expensive asset to strangers for 3-10 days or whatever.

Hi Chris from the U.P. of Michigan.Congratulations on deciding to get into real estate investing with your first Buy, Rehab, Rent, Re-finance, and Repeat or BRRRR and you are wondering where to start and who you should add to your team first.It is good you have cash or cash equivalents to buy the property and complete the repairs.As far as who to have on your team first, I would say an investor friendly Realtor who can help you find deals and introduce you to the rest of the team like a good property inspector to hopefully let you know about potentially expensive repairs early before buying the property so you can buy it well or not buy it at all.

You should go through an RMLO if it is a homeowner who will live there.You are doing a wrap loan.

With your point, it seems like living security of 'where's next' for them will be the biggest obstacle for the seller to overcome.

I currently live in Denver but am looking to move to a new state.

@Mike Grudzien @Tim Delaney do you guys think it'd be worth joining a credit union in the city I used to live just to get the rate even if I'm out of state now, will they still give a better rate? 

Each tenant living in a building has their own unique rent amount, so even if they do not leave a notation with the rent payment, I know whom paid the rent based on the amount alone.

I am still living in Chicago but plan to move to New York in a year or two.

That is, buy one home in city X (where I don't live), live in it a couple of months let it be an STR the rest of the time and then the next year (or in two years) repeat again in the same city. 

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).