Remember, if you sell it, you'll have capital gains that you will have to pay since you are buying the other property before you sell you're old house.

How much is this individual paying to park a trailer there?

Quote from @JooYung Choi: You could consider going for a STR in a vacation market that will give you way more cash flow to pay off the HELOC quicker.

One year ago, I was hired to help a landlord whose tenant had stopped paying.

Is she paying a property manager?

They are lending to people who are so desperate they will pay 16+% for the loan.  

Well, how much is the lot for sale for?

I have cheap guys who do it 1/2 to 1/3 what you pay if call someone off Yelp.

Montgomery Metropolitan Housing has a reputation of being difficult to work with and are slow to pay at times r so I have heard.One thing to keep in mind is that even with section 8, you still get to set your criteria that tenants need to qualify for your unit. 

I am not saying everyone needs to pay for a mentor....there are multiple ways to get into the game.