- Do you want an ocean view, or is proximity to the water or to resort amenities like fine dining or shops most important?

all units LTR, or some units other arrangements (STR, MTR, rent by room)? 

Paid a top local esigner to come have a look and all she did was insult our cute little place that was doing just fine.....But I think where a designer could add value is by suggesting unique areas, like game rooms, coffee bars, outdoor BBQ/play areas, and stuff like that. 

Try to put a bigger down payment in than you might need to give yourself some breathing room.2.

Tenants save money when using a shared meter, so there's plenty of room for error when calculating how to distribute the charges.

I previously lived in this property and never locked myself out of my room so I never looked nor do I even know if I have a key for the bedroom door.

house hack in some sort of fashion.Either buy a duplex or large single family that you can rent out a room/side of the houseOr buy a fixer upper in the best neighborhood you can afford. 

As I see it, the only ways that real estate pays you well in the first 3-5 years is low to no leverage or a strategy that requires more work (short term rental, mid term rental, rent by the room, etc.).  

A grand negative cash flow is not the issue.

If you remodeled, added a room, replaced a roof, painted, boosted the curb appeal, etc. that's a different story.