I am not a CPA, so check with yours first, but I believe you are able to file a forms 3115 and 481a (change of method of accounting) which allow you to claim previous year's depreciation without actually amending previous years tax returns. 

Maybe asking about the time involved and legal fees so far can help set the frame of my offers.

I understand there are risks involved and being a landlord is a full time job; but what I wanted to know is if it's as bad as naysayers say it is.My dad thinks I should do it and said he wishes he did that when he was young.

Once you move past the owner occupied I would say is when the game changes and you will be looking for a bank that will lend more on the property and risks involved beings it will be a true investment from the banks perspective. 

I want sufficient insurance, but if something catastrophic were to happen I would construct under more modern building methods.

And I’m looking to get involved in these rental properties .

It is one, but it also makes getting involved more inviting and friendly. 

How do I sell my property what is the procedure, seller and buyer commission, why does a attorney need to be involved etc?

Even with a regular 203K you might only be able to do it if there are safety issues involved.

HELOCs do have significantly lower closing costs but if you use one for the down payment, you will need to have a method of paying it back relatively quickly.