I usually do a "drive-by" and check for obvious big ticket capital items that could turn any numbers sour quickly.a. 

@Jay Hinrichs As always, I appreciate your perspective.....and don't get me wrong, I truly do....and I follow and respect your views in REI......Also, I buy a lot of books, diverse disciplines and not necessarily only REI, so when I said I could get a lot of stuff free here, I meant that I could learn quite a ton from folks who know better than myself and more experienced......In fact, I had been to a 'guru' seminer and with my flight ticket and travel expeses, I must have coughed up almost $10k!..

Cosmetics seem fine, but are there any big ticket items that typically cause more of a headache than necessary? 

The million dollars you'll save by investing outside of SF should justify a few plane tickets :)

We've had a few surprise big ticket repairs (electrical, plumbing) in the past couple years, and right now considering what to do about a tub that needs to be replaced.Our cash flow is pretty thin (about $100/mo), and accounting for the repairs it is clearly negative cash flow. 

I am also curious how people look at capital expenditures and whether or not that budget is part of paying for maintenance replacement items, or just for big ticket items like roofs and furnaces.  

As for maximizing your funds, as is mentioned a lot in Set for Life, you need to really look at the dollars you're spending, not the small stuff at Starbucks or that type of stuff but the big tickets items like your car payment and see how you can minimize your expenses.

I have a friend looking for 2 BPCON 2022 tickets.

Homes are a big ticket item. 

If you are concerned about the maintenance or repair costs of an older property consider buying condos, the exterior big ticket items are covered by the association not individual owners.