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. 

This is $35 per Sq/Ft plus another $5k for an additional big ticket item.

, free ski lift tickets, season tickets for????

Im not that experienced but noted down the big ticket items this one needs (didnt do an inspection but only what I was able to writr down):New kitchen setup for both units.The roof was leaking which caused damage to both kitchens.New roof.New heater unitNew floors I think it also need to have the bathroom on second unit redone.If you know what you are do it and have the time to invest maybe putting 30kto 40k for rehab this might be a good brr property.

Additionally, plane tickets are more expensive here than they are in the lower 48.

Tickets are going quick but you can find details in the meetup tab on this website or I'm happy to send you the link.