My backup plan is to purchase more condos (~200k/each) which gross about 45k/year (net just over half that) and save up until I can afford something bigger.Ideally I want to stay in the same city with the multi and do a combination of long term and short term rentals.Thank you for your time.

, but if residents in that area are already paying those "expensive" prices, should you place just below to grab attention, or stay within that prices ball park for your property? 

You need to know three things:1) What the market rent is2) What amenities the average unit has at that average rent3) What is your tolerance for an empty unitIf your rent is average and they just want a discount stay the course you may get a call back once they've shopped around. 

She didn’t break the lease and over stayed by one month.

They need to maintain a certain number of listings to stay at the company, otherwise they will get fired.

My goal is to cut on the amount i work and stay home more with wife and help raise the baby. 

The FHA appraisal I believe stays with the property for 6 months.Ask the buyer to split the difference or make up the difference if they want the house or pull the contract and re market the property and sell as Conventional financing only.

If there is a mortgage attached to the property there's a 99.99999% chance there's a clause in the mortgage that requires it be paid off when you sell - regardless if it's in your personal name or an LC.Yes, it does complicate things when doing 1031 - but not really... there are rules you have to follow to stay in compliance with 1031. 

We will stay in the middle for the entire term, pay the rent every month (even if the house is vacant), and be responsible for ALL maintenance and repairs under $500.

I would stay close to the development and near the light rail.