@April Causapin I love that you're taking a look at investing and moving yourself further out the risk curve! In regard to your comment that you are "a very conservative person in terms of finances and gets scared when there’s too much risk," what are you considering as increased risk? In my opinion, a higher purchase price isn't necessarily more risk. To exaggerate, if you were choosing between a $1MM apartment building in Santa Monica that rents for $10,000 per month, and the the property you listed above for $400,000 which would you choose? From my perspective there is a lot more safety from a property that has better debt coverage and higher desirability. You might find in your area that you'll be taking less risk buying a larger house for $750,000 than buying your smaller house which I think you're concerned about having a small lot and interior square footage.
For your cap rate calculation... the cap rate should be the (net operating income) divided by the original capital cost or the current market value. Your expenses should not include debt service. Basically the cap rate is going to tell you what the property would yield if you bought it cash.
As far timing the market, I think it's so difficult to do that I don't even worry about it. I mitigate market timing risk by being in the market buying good properties every year for the rest of my life. To me, now is always the best time to buy.