You can't work on the property as it must be a passive investment (e.g. you must hire someone to fix the toilet and can't pay the expense with non-retirement funds).7.

Had a few were I let the attorney dictate when to hire the abstractor ( usually about a week before closing) only to find out title was buggered and i spent a few grand on plans and due diligence.. so learned my lesson there   

Due to that, there are a number of agents who hire their colleagues to represent them because of the liability involved. 

We have a tenant living there now and the rental agreement with the tenant was through our LLC and the property management company who is dealing with the tenant was hired through our LLC. 

I did about 80% of the work and hired out a few odd jobs and all the drywall (ask me about my drywall guy!).

You will typically need to hire someone to skip trace the list for you in order to accurately find contact information for the owners. 

Once you narrow down the market, be sure to hire an experienced realtor that is knowledgeable about the regulations in their vacation rental market so that you can find the right property in a rental friendly neighborhood. 

Does it matter whether I manage the property myself or if I hire property manager?

Who did you end up hiring?

That made me think that I was ready to Hire VA's without the proper infrastructure in place.