On one hand a SFH property in a good location, with the right rental price will be rented in a reasonable time frame and have a lower turn over rate.

In fact you would arguably be in a hell of a lot better shape spending that $300/mo on a sub to property than on stocks when you factor what rents will be like in 30 years, the savings you achieved during that time frame, the fact that the property is now paid off completely, etc.

The next metric is return on capital based on projected refinance time frames.

@Han YuI agree with Kevin Hunter, sounds like you should sell.Maybe try FSBO(depending on time frame) and if not a discount broker might be able to save you on fees.

So, long story short, I am confident that my with holding of a portion of the security deposit was correct and accurate, and that it was done in the lawful time frame. 

That said if I got a property within that time frame I know I could easily find a tenant but it would sit vacant for 5+ months.

I believe Wave is free and can connect to your Credit Card/Bank Accounts and feed in expenses which will make the expense tracking process easier.  

Some of the most successful investors are in expensive markets (LA, NY, SF, etc.)You just have to understand its a different approach.

What's your time frame: Are you looking for short-term (<1 year) deals, or are you OK making loans that won't pay out for 5 - 10 years?

Try to find a way to get the payback time frame down and you will have much better luck.