@Jeff Copeland completely random...I love your logo.

These random maintenance costs are going to keep eating you alive as a landlord.

To our surprise, some random lady opened the door (who is not supposed to be there and was high as a kite)... asked my dad who he was and after introduction went inside to confirm discuss with our tenant... came back and said that the tenant was not home and to come back after 5pm.

I would not entrust it to some random tax person if I were you.

I would rather have the A/C guy I know and trust fix it first thing tomorrow than call some random emergency repair company. 

I’m okay with spending time finding a manager and doing the random tasks that turnkey companies overcharge for, but I don’t want to spend dozens of hours trying to buy below retail.Basically, I want to pick a new-ish construction house off of the MLS, negotiate to roughly retail price, do the due diligence, get a managing company, and get on with my life.

I have had  them take stuff, but to me the worse was when they spray painted the kitchen cabinets and smashed random sides of the cabinet, cracked the glass on the stove, spray painted the inside of the frig and oven, cracked the blocks of the patio and left the spilt alcoholic beverages and ladies underwear all over the hardwood floors. 

I don't talk to random employees3.

Google searches have led to randomly clicking on every link in the results in my search.

Benefits of replacing upfront would be:No hectic service calls for me, the property manager, and the tenants when they randomly fail in the middle of the winterI can capitalize the expenses if I replace upfront vs treating them as repairs down the line It'll increase the appraised value, so I can basically pay for the cost with a mortgageThe only argument I can think of for waiting is "don't fix it if it ain't broke" -- might as well just save the money, and who knows they might last a few more years.