That's good at handling wholesale transactions?

I would think you should be able to do an affidavit stating you are an owner occupant and get an exception if your mortgage broker is savvy enough and knows what they are doing also try calling another local mortgage company/broker that's not a bank they tend to have better contacts with underwriters and can get this handled easier than say a bank.

I want to start off this way because I think it's easier for me to handle, since I'm doing this on my own.

If that property passes a rigorous due diligence process and you choose to pursue it, I think, as a new investor, your best strategy is to figure out if it would be possible to buy the 2 acres with the duplexes and sell the other 8 acres.You can get up to speed on handling those or hire a PM a whole lot faster than you can figure out how to develop raw land. 

Also, I'm not sure whether it's best to let a property manager handle the repairs (do they do that?)

They should be able to handle everything for you, including... 

As for attorneys, the realtors will handle all you need to know.

I have bought homes listed on hudhomestore but still needed a broker to make the offer and handle the sale.

How should I handle this.

I would think if I had a fire, I would notify my insurance and let them handle it, much like an auto policy?