Make sure you are accounting for HOA as that is a big expense.

Our HOA covers the exterior but the contents were ur on a Lloyd’s policy. 

The good thing about a condo is that the HOA handles so much.

I have it in my contracts state that the tenant is responsible for yard maintenance and it must be maintained to HOA standards (HOA exists in my case) and provide no further details.

HOA $650 very desirable community and that generation is financially responsible and units are decently clean upon leaving.

Once I was able to confirm that the HOA would allow me to rent it, i locked it in.I have a couple other SF Homes that I rent to a single tenant or family. 

I see an opportunity to help her try the move and also set up as a future rental if after a year she cannot manage.My struggle is there is no solid information regarding HOA rules across all the 55+ communities.

However, not one of the units in question is vacant.Are they legally working around the HOA rule? 

Trying to figure out if I, as a buyer, am to pay this $200 "initial assessment" to the HOA? 

Depending on how much you are paying to Airbnb in fees and how much you are paying to have the unit cleaned and or managed, it may be possible to cash flow using Airbnb but you would need to evaluate using your Down payment, interest rate, monthly HOA etc.