Here, we were after an asset we could pay off quick & cash flow aggressively.

Hi I’m interested in a vacant property and know I can look up the name on tax records but won’t necessarily be where I can contact the property owners.thanks in advance.

Otherwise you would take title to the new property as two LLCs with one of you as the single member of each.You've got a very good scenario to get some of the proceeds tax free and defer the tax on the rest. 

If he doesn't make a decision - in writing - then he is required to serve the remainder of his lease, or has to pay a penalty to leave early.

Expenses: $1,225 (Mortgage, taxes, insurance property management)Rent: $2400Cash Flow: $1,175Overall I'm looking for a low barrier to entry, and will be screening prospective tenants myself so I'm not too worried about the area being not so great.

I was happy to see you said your current bf would "pay you rent" as opposed to buying the house together.

The COC will be right around 8%, with $500 in cash flow (after accounting for Maintenace, repairs, taxes, insurance, vacancy, etc.).

Do you know of any situations where property taxes are increased exorbitantly to shake loose undeveloped property?  

They also mow the lawns, shovel the snow, pay most if not all utilities, and provide most of their own appliances. 

Get to know who are doing business with and never pay an upfront fee.