There is a place and time that it makes sense, but as long as you get any cashflow that first year, father's time will likely help you out after that as long as you have a quality product. 

It may not make sense for you, however.

Am I suffering from greener grass syndrome, or should I have "Lived where I want to live and invested where the money made sense."?

Hope all of that makes sense.

Of course, this makes best sense if you can make an agreement with the seller before buying the note.

@Rachel Seymour-NewtonIf the smaller property is a strong deal with solid cash flow and tenant demand, it could make sense to buy now and start gaining experience.

.: Hey Steven, thanks a lot for the feedback, this makes a lot of sense.

Yeah that makes sense. 

It’s an uphill battle with the city; many investors can look at this and see that this only forces appreciation and get in even though the cost to play is high.Hope that makes sense.

That’s the key benefit.As for the cost segregation study, whether or not it makes sense really depends on your tax situation.