@Jesse S.As a fellow Brooklynite - I agree that investing in NYC can be challenging.If you do decide to use a turnkey company - make sure to spend the money to take a flight and meet with the turnkey provider.

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.  

We live on the east coast and would love something accessible by a short-flight and would be reasonably easy to manage from a distance.

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.

Don't tell me if you got an applicant that was a flight attendant, pilot, hotel sales person, Disney employee for 15 years, etc, etc - that you would have denied them.

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????