How do I decide if I'm over extended or just think I am?

[Marvin Valencourt]

Since I'm using this as a first and introductory post I'll warn you up front it may be a long one. ;)

First some background. I'm a newb at the "investing" part of real estate. I've owned my own homes (and lost one in a divorce) for about 20 years in solidly appreciating markets. I was fortunate enough to find a REO deal after the divorce and shortly thereafter the market really took off where I live in FL so I have a fair amount of equity in the property even ater a home equity loan. As further incentive my mother passed away a little over a year ago and left me a small sum of money. Since I have a decent job and credit score and little secondary debt I've decided that it's time for me to start acquiring rental properties to help finance my puttering after retirement in about 10 years or so. After much reading, "observing" and researching the current inventory of possible rental properties I ended up writing a contract on a leapfrog house last week and the financing is pending as I write. I've also made another "acquisition", a real estate attorney that I think I can trust. My intention is to go ahead and rent my current house. I understand that being a landlord isn't the easiest thing in the world but I *think* (remember I've never done this before) that the market will bear a rent ~$300/mo over the costs of mortgage, HE loan, maintenance and taxes and insurance. I also have enough cash left to possibly be able to purchase another low end property - a trailer on 2 lots in an area that I expect to join the "boom" within 5 years - without getting too creative with the financing.

Now for my problem - how to decide if I should just stick to taking the baby step of the leapfrog or go ahead and stick my neck out and buy the second property? I read where most of you have regrets about the deal you *didn't* do and the investor vs. observer thing but I'm still having trouble deciding how to convince myself to leave the relative safety of knowing I can make all my payments to letting other people make them for me and worrying about what happens if they don't later on. Commments and suggestions are appreciated....