Anybody buying up old property out there right now is paying $300k+ for a run down shack that needs to be razed and build a McMansion/vacation rental in its place.

When I first visited the property, I can tell the owner had neglected to keep the property updated and let the tenants run things.

My business partner runs our flipping/wholesaling business in Chicago. 

But the problem is that the current HOA has no legal representation currently no board, no valid address etc. now another investor came in and bought about 70% of the units and they plan on trying to get the HOA up and running at the annual meeting in February.

I tell you this, because you would be far better off designing your own DB, as no on the shelf product, will have everything you need to run your business efficiently. 

There is a monthly meetup run by @Nathan Mairs you should check out that had 6 great people at it last time.

The article says 20 bids and the winning one "wasn't an outlier," so we have good reason to believe the sales price is ballpark accurately telling us true market value for the home, without even having run comps.Really, what's more likely at play here, is a listing agent that wants to be able to juice up his "average % over asking" pitch a little bit more for future listing presentations.

But I keep hearing people telling me not to rent out a property with a swimming pool because of insurance/liability issues.If I intend to insure it fully, am I still gonna run into problems?

I assume you already have an LLC set up and your income is running through there?

I personally have run the numbers on around 15 apartment complexes in the Phoenix metro area and I'm looking for someone to bounce numbers off of as a sanity check.