Brand AwarenessAlthough, number 3 I could argue is more important for future years and not so much right now as I'd more concerned with further cementing our business structure, working out systems in all areas of the construction, reconstruction, and rental arenas.  

As far as I'm concerned, that's money that the deal dictates I need to set aside and ideally will never touch again, so I just add it in to my up front cost.

Again, if the units had central air (something I will consider adding in the future) I would not be as concerned.

I develop towers throughout the US and I could probably help you with some of your questions/concerns.  

Based on what you are describing and my knowledge of the area, I am concerned on several fronts.  

My concern is that I want to get the process right.

Many of the concerns that are voiced today were also talked about back then, but I decided to make the plunge.  

The HOA rules are strict, and as an owner of 7 units I would be part of the HOA board which makes decisions concerning repairs/upgrades/expenditures.

@Trevor Ewen  I'm sure it's just me but as a buy&hold investor, I'm focused on the performance numbers of the property and not concerned at all regarding tenants. 

When posted the question,  I was more concerned with how easy/difficult it would be to secure conventional loans after having multiple mortgages.