Do players with real VC backing want to take that amount of risk at this point in their lifecycle while growth is still occurring at a steady clip amount accredited investors?

Some of those items get replaced once per life-cycle, so if they are new, you typically don't have to worry about them again.

Many people aim for a 10-15 year lifecycle on Windows.

All answers are function of your investor and life cycle.

When I  think older buildings, I think of major mechanical items that need to be fully replaced over time to meet current fire code or modern amenities that are expected or reached the end of lifecycle before they fail.

@Dan Heuschele I used the same spreadsheet that does the whole Lifecycle Cost Analysis thing.

Also the Lifecycle Building Center near the West End https://www.lifecyclebuildingc...It's a crapshoot as to what they have but ususally at a minimum a good source for sinks, doors, toilets and large appliances

It's a full property management lifecycle platform, so it does a lot more than just collect rent electronically. 

I can think of bookkeeping (entering P&Ls into QuickBooks or spreadsheets), making our Expensify reports... what else in the real estate asset management lifecycle could we outsource? 

There comes a point in every investment's life cycle where it becomes more advantageous for you as the investor to trade up.