The outline of Sheppard Estates is where the subject property resides (red square).

With a tenant, I was paying ~$50/month and hoping that nothing broke so that I didn't go any further into the red.

I hear it is much like Poker, as I know nothing about Poker the real players I hear are not looking at each hand they win or loose on, but what did they accomplish during the whole season or year.

Is the ole yellow letter with red ink thing really the best way to go about it or could I try blue ink?

If you cant fund the whole deal by yourself I would bring another player on the table.

If I go longer than 5 months, I feel I will be in the red and underwater on this deal.Should I get 2 places for $55K each?

You didn't mention what budget you are working with but you may wish to look into Casselberry in the Red Bug Lake Rd area.

Sure, rates may be higher than what you'd get from a traditional bank, but you'd close quickly, avoid the red tape of a bank, and they won't care about your daughter's trust.  

I would make sure you get a contract with a signature that specifies exactly what colour they want (ie Firetruck red from XYZ company) not just red, otherwise when it's on the wall and it doesn't look like what they thought it was going to look like it might be an issue.

There's a few players in my area with 1 LLC and like 50 properties in them.