If you slip up in this business the LAW will remind you that ignorance it no excuse.So bear with me as I alter my perspective and thus my approach. 

This way I will know how I can approach this owner about this property.   

From a very high level approach, the less buildings you have the less underground work you're going to have.

My strategy is to build my rental properties for a long term approach rather than any short term gains.I tend to get into the weeds of things, but I like to have a full understanding of everything and have a full thought out strategy.

Banks, particularly large institutions, will usually not budge if you approach them about a specific property.

Should my first approach be with a letter written by me or by a real estate attorney?

Most are off-market.If you are a retail property owner, how would you prefer someone approach you?

I love to hear that you're taking the independent approach to self-managing.

Best source for this question if you really want to be technical is your broker (but I could see why you wouldn't want to approach them) or an administrator of your association. 

Do you prefer a longer term approach with rental properties?