@John Thedford good idea.

Some HOAs will limit the units that can be rented ...connect with a condo specialist  realtor and you should get a good idea of whats possible ...if you will need a loan - get pre approved ...loan pricing for a 2nd home is  similar to pricing for a rental property

I had been busy doing other projects and this place was on the low priority.

@Tabitha Price great idea to explore this!  

I would call some local leasing brokers in your area before you have any non-refundable earnest money to get an idea of the tenant demand for something like this and if you are new to retail leasing/investments I would highly recommend you hire one of those brokers to negotiate the lease for you.

Set up the LLC business bank accounts.Moving to an LLC increases costs, work, and complexity.

You will need to be spending 2-3 hours per day on the business in the beginning.

I would be the first to ask for this "advanced" type of tracking but I feel with out it you aren't treating these units as a business and are guessing.

I really like the idea of starting with higher frequency, and early inspections at first.  

Business groups for face-to-face meetings ?