As you research, pay attention to the short term rental regulations in the city/HOA where you are looking. 

You do not have control over whether you can lease the unit or not over time because the HOA can set restrictions on the number of units that can be rented2.

Knowing what I know now I am more inclined to purchase a property that is cashflowing a higher amount in an area that has less costs of ownership ( property tax, no hoa, etc etc)What would you do if you were in my position and why? 

We are a part of an HOA community with about 100 other townhomes in our area. 

In your situation, renting out the other rooms would be a great way to get your monthly payment down to much less than renting a 1 bedroom apartment.Another thing to consider is the HOA.

Ordering payoffs and HOA docs also require time to process.

I don't know your area, but using the four square method, charging $1800 a month seems too conservative if you haven't calculated taxes, insurance, HOA fees, etc. cap ex, future maintenance costs etc. 

Watch out for high HOA fees and low owner occupancy rates that can make it hard to get financing.If you are looking for an off-market deal maybe start with absentee owners that have owned for 3+ years.

  $300 a month cash flow on a condo is just one hoa due raise from being negative.  

I assume this is an HOA rule?