As an investor, you should only make numbers-based purchases.Also, agents are only transaction-based - if they make a mistake (or choose to take advantage of your naivete) they still get their commission check and can disappear:(So, a great PMC is often the best choice to start with, since they obviously know the rental market and they have to deal with whatever they help you buy, on a daily basis after the purchase!

Also, most investors are every day people looking to rent out a second home.

Realized it would probably be cheaper on a monthly basis to have a mortgage there rather than pay rent for another year.

There is an amount of money I'm willing to give up to NOT have to deal with my tenants on too regular a basis. 

Get one as you will receive stepped up basis for tax gain purposes.Next decide with your sister on the plan.  

My question is whether this will this cause issues with setting up the purchase price as the cost basis and depreciating the property accordingly?

But, that doesn't mean you need their help on a monthly basis.

What Galen is saying is that you are taking your original basis out first which is not taxable. 

I can that zillow is generating views close to 10 every day but no contacts so far.How do you approach the situation when there are no comps for your condo?

We're thus able to evaluate our rates, and keep pace with inflation, on a monthly and quarterly basis.