Save a "reserve" so you can handle vacancies, maintenance, and all the bad things that pop up when first buying an investment.My recommendation is that you read a book like "Set For Life" by @Scott Trench and get your financial house in order so you go in prepared.

If annual maintenance can save me from replacing the deck in 7-10 years, and is relatively inexpensive, then I'll consider buying.

The majority of my tenants Tend to be higher maintenance and expect more for less service babe it’s kind of that entitlement mentality.

So I started looking and within 2 months bought my first Short Term rental that I manage myself over airbnb and have a team to work the cleanings and maintenance.

If the layout is good so that you don't hear or see each other (good privacy) and you get the right tenants: (low key/low maintenance-people you'd hang out with as friends) newly married that work or go to school all day and just sleep there make it a breeze!

I self mange the properties and rely on a whole bunch of different maintenance people but the Plumber/HVAC guy is the guy you need. 

If the layout is good so that you don't hear or see each other (good privacy) and you get the right tenants: (low key/low maintenance-people you'd hang out with as friends) newly married that work or go to school all day and just sleep there it's a breeze!

The buyer is responsible for all taxes, insurance, maintenance costs, etc (you would be named the beneficiary of the insurance - fire ins, to be clear).Yes, you should get a good size downpayment. 

Ask a real estate attorney for the state you are considering.But, here are some costs:Unpaid principalArrearslegal fees of the pre-foreclosurehome owner's insurancemoney to the seller for movingmoney to the real estate agent if one is involvedtitle insuranceescrowpre-paidsunpaid property taxesunpaid 2nd loan if it existsunpaid electric billsunpaid water billsunpaid gas billsunpaid mechanics liensunpaid fines for city violationsdeferred roof maintenancedeferred maintenance in generaldumpster to get rid of everything left behind

Vacation Rentals are high maintenance.