I have a couple of investments and am about to jump into a Short term rental while still being a w-2 employee.

@Daniel Amsalemhi. i see this thread is a couple months old. 

I've had a couple of SF rentals with pools. 

I own a couple of places in Playa Potrero which is just north of Tamarindo in Guanacaste.

I’m a 28 year old married man with a 3 week old son.

We focused on where we went wrong with the first couple of homes we purchased.

The key difference, though, was he spent months carefully getting to know the local architecs, reputable builders, and even a couple of niche design firms that specialize in modern builds for mid- to high-end buyers.

Years go by and eventually Grandpa gets tired of fixing porches, nailing gutters and steam cleaning carpets that 'have a couple more years in them. 

Quote from @Shayan Sameer: I would reach out to a couple lenders see if you can get some competitive rates and also see about the points too that they are charging..

The rental market is strong due to students and digital nomads.Managing a couple of tenants would not be too hard but managing a dozen, on the other hand, would be a nightmare.I am a bit torn.