Help Needed: is this a good investment in today's market?

[Aspen Jay]

Hi! 

Just went into contract on a home (3 bedroom/2 bath with an outbuilding in the backyard with power) yesterday before doing solid number calculations (I relied heavily on my agent making the mistake of not doing my own due diligence, even as a rookie, I should have known better!). 

Using the biggerpockets calculator, the numbers just aren't weren't adding up. Cashflow wouldn't happen until year 6. We planned on using this as a STR and were expecting 50% occupancy. Talking to my agent, who has three of his own short term rentals in the area, tells me, my calculations are ultra conservative and the numbers do add up for this area. House values in the area have increased about 5% the past year and the Greenville area and surrounding areas are rapidly growing.

The monthly expenses (including utilities and 5% for repairs and 5% maintenance) come out to $2,291. A long term rental in the area would rent for about $1,800 a month, so as a backup that wouldn't be a great option. STR with a 50% occupancy monthly income I'm guesstimating to be about $2,037. So a $254 loss. Granted as we built up momentum we could probably get it up to 60% (that's what my agent says he gets) or perhaps get some MTR revenue working with insurance agencies.

Where is the disconnect? He has done short term rentals, I haven't. He said it should start cashflowing in year one and that I will miss out on all that appreciation if I don't jump on this. Is this as good as it gets in today's market and I should move forward with this investment?