I don't know your market, but I'd bet the $400-$800 rent range is a tough market for a newbie to manage rentals in because the tenant class could be challenging and because maintenance, capex, etc. may end up eating a lot (or all) of your cash flow since there isn't a whole lot of rent to cover those items.

Could be anything from someone leaving a faucet on, bad ring on a faucet to a leak or all the copper was cut out.

You seem to always refer to those who were irresponsible investors, uneducated, foolish, or all of the above.

In Madison, you will be competing with 20% or all-cash buyers, especially for the first-day-on-market HGTV remodeled homes.

As far as tenants, while we self-manage, we had our realtor find us tenants, and we'd pay her half or all of a months rent.

I've got two offers out and one more before tomorrow =) One or all will be my first purchase.

Question: Is AirBnb a noun, verb, adjective, or all three?   

Have the seller hold some or all of the note to get into the property and chances are the other issues will not factor in.

One of the highest property taxes in the country, Try KC or Al - very low property taxes :)

You may not have as much luck with buying from investors on a competitive product (duplexes), but if its been sitting awhile or needs a lot of work, negotiate some or all of your closing costs into your offer.