I would rather have the option to quit my job based on my success in RE, if that makes sense.

Thus, I need someone competent to do a thorough financial analysis to help me understand where the swing points are in the tradeoff where one option would make more sense vs. the other one.Something along the lines of:https://www.nytimes.com/interactive/2014/upshot/bu...but which also incorporated my current investment property holdings.

I totally agree with you, Anthony, and it makes much more sense to me now after reading your response, so thanks again for sharing.Another long-term goal of mine is to own and operate a vacation rental in Orlando/Kissimmee.

Now granted this is not money in your pocket but if you are planning on keeping the property long term, does this approach of taking advantage of the FHA loan to buy a property you wouldn't dream of buying right now because you lack the down payment cash make sense to do?

Since all units need Rehab, and now tenant is moving out, it makes sense to do the whole unit while it will be vacant. 

If you find a property and the numbers make sense, buy it, if the numbers work jump on it, I do agree that it is better to have a tenant in place if you are buying in the winter, a property being vacant should not be a deal killer if the numbers work.

If there were no vacancies or capex this year her cap makes sense for 1 year... you use your numbers as leverage to lower the price.

My goal is to house hack with my first investment property, but I'm open to going other routes if they make sense.

The real inflection point comes at around 75 at which point it makes financial sense to hire on-site property management.

If you want some retirement money then it might make sense to invest in a few SFHs.