If the HOA is ran down with a bunch of vacancy you can expect to pay or eventually pay higher HOA fees from the lack of owners paying into the pot.  

The only hitch is you have to setup a credit monitoring service with them for your personal credit, then I think it eventually switches from being backed by you personally to the entity's credit.  

Don't be afraid to pass on a deal that isn't good enough, but eventually you have to pull the trigger.

My goal in real estate is to build capital in the short-term through wholesaling to fund future fix-flip deals and eventually build a portfolio to create substantial passive cash flow.

Eventually you should move totally away from any properties that will not appreicate.

Eventually I would like to grow into commercial real estate which has always fascinated me since I was a child.

I think if you're eventually planning on making a business out of this, just like any business, you're probably going to want to create some sort of entity sooner or later.

Call around to both roofers and general contractors, explain the situation and eventually you should find someone who will do that type of project.

We eventually want to sale the home and would like advice on the thought of this.

It does make sense.Pro's:Higher earning potentialYou own your own businessIf you do it right, the business can eventually operate on its ownYou can have a property management division in your business and have it manage your investments as well as others.Cons:Lots of workYou won't have as much time to put toward making deals as a brokerThe business may not be successfulI recommend you do it but it will be more work and you will be risking your own money you put int the business.