HI we are Canadians investing in the us we  invest in Detroit and toledo where we have great teams on the ground including trusted property managers who take great care of our properties.

You should definitely be able to find decent multifamily properties for under $200k, and multifamily would be my suggestion for starting out if you can swing a larger down payment (depending on loan type, you MAY need 10% more for a multifamily vs a single family, but not always).

I have been saving for a down payment on a rental property.

There are some areas near Gatlinburg I would consider, but cities are just a large HOA which I do not trust over the longterm.

Either1) your startup takes off and you can distribute profit fast enough to pay off your debts, or2) you find another source of $100,000 a year (which barely even starts to pay down the $300k, but might provide a better chance for a better loan), or3) you BK and possibly lose the rental houses to creditors (hopefully not, but we don’t know how they are held), or 4) you sell the houses, take the tax hit, work with the IRS on a payment plan whose interest will be much lower than your CCs, and focus on the startup.  

There best move would be to put the property in a trust and not sell it until after the current homeowner passes away as that may allow the daughter to get a step up and then sell.Also, seller financing does not always net the highest price - and there is the issue of the seller having now to hope a loan does not go into default. 

I advise you to go personally and/or find a trusted local person.

I haven't heard of the bi-weekly credit card payment idea.

Then you can talk to the mortgage company or payment processor yourself. 

I know them well, I like them, and I trust them.My wife and I have purchased a wide range assets from PPR.