The agent says that conservatively I could bump it up to $1600-1800, with it being at $1400 would you say I should try to increase it to $1500 for next year and steadily increase it from there or make the bigger jump straight to $1600+ and risk losing the tenant?

Correct - Track all your income and expenses.The bookkeeping will determine whether you are profitable or not.it will also be good to compare from year to year your income / expenses to see what expenses you can potentially try to limit.I.E.

So now I'm faced with the potential of loosing EVERYTHING job, house, car, wife...Finally I stopped focusing on what was wrong and focused on the solutions. 

You'll have a property manager do the management (so you being close to it is not needed).Yes there are risks for some people to go out of state but if you learn the techniques like I have, you'll see it's actually easier and far less risky.

Quote from @Reeti Peshawaria: Hi, I'm in the process of learning about short-term rental investments and analyzing potential markets, but I’ve hit a major roadblock: understanding local regulations.

If it's a long-term play, the potential savings on PMI with a conventional loan could be significant.Have you compared rates for both options?

Also, I have yet to see anyone discuss call risk with these.

You run the risk of offending tenants by asking them to jump through hoops again just to renew a lease. 4.

Investors love to take advantage of this strategy to expand their RE portfolio and have better appreciation potential.

It checks all my boxes for potential.