Ive used hard money and conventional financing in the past; however this one has numbers that wont work for those and was wondering if there was an option to create a win-win for everyone.The home is currently valued at $70k conservatively and is in clean condition (just an older roof). 

On the first one the guy never cleaned out the garage so I charged him $50 a month for a few years then offered him a payout in exchange for a payoff deduction. 

I submitted a written offer today for a property in a neighborhood close to where I live.Here are some of the details, please let me know your thoughts, however harsh they may be...Purchase Price: $295,000 (Seller is absorbing 4% for closing costs)Down Payment: $0Gross Potential Rents: $24,000/yr ( I feel that these numbers are a little low for the area)Expenses: (Let me know if you think I may be missing something)Property Tax: $3,800/yr ( I may be exempt in Oregon for have a disabilty from my military service)Repairs/Maintenance: $2,400/yrInsurance: $600/yrUtilities: $2,200/yrTotal Expenses: $9,000 roughly per yearNet Operating Income: $15,000/yearDebt Service: $16,500/year (roughly)I am trying to get the price down to $285,000 after my walkthrough and inspections.

You have to make sure your roof, HVAC, furnace, appliances, plumbing, electrical, foundation, clean out piping to the street, etc are all taken care of and get a full inspection report. 

clean well maintained successful business paying regularly?

Look it up here on BP if the term is foreign to you.If your finances are in order (clean on paper), explore what programs are available to you for a primary residence.

While escaping the harsh Canadian winter I could manage the investment properties more hands-on.

good schools, low crime, rents moving upward, places people want to live, residential areas, clean, modern.

Additionally, if they have income, credit, little debt, clean car, and are clean looking then that reinforces my gut feeling.  

It is common practice for them to pay the 11.5% for Walton and Okaloosa counties and 12.5% for Bay County, and the renters pay the cleaning fees.