You're definitely on the right track in terms of looking at real estate investment in the context of your own personal tax and financial situation.

If you haven't already done so, I'd encourage you to discuss with your attorney and accountant the best way for you to hold title to your investment real estate so that you're protected from a liability standpoint and protected from probate and tax liabilities should the inevitable occur sooner rather than later.

That of course, assumes that have selected the most appropriate and qualified CPA and attorney for your situation. I have an attorney that I use for wills and trusts, another for tenant evictions and collections, and another for real estate specific contracts. Although I could use one attorney for all of these functions, I would much rather have a specialist that does it right the first time and doesn't have to spend his time (and my money) researching areas that they are not familiar.

The same goes for CPAs. My primary CPA handles my personal and business and tax planning and tax returns. (Note: If you're not meeting with your CPA at least once a quarter to plan then you're missing huge opportunities to save on taxes.) When I'm reviewing the viability of an investment property I don't send it to my regular CPA to review the financials - I send it over to a financial analyst and a real estate economist that can not only confirm the numbers but give me an objective indication as to where I could potentially cut costs and increase revenues. A general CPA would not have the critical market knowledge to provide insight into the numbers.

Although you wouldn't go to that level with the analysis of an SFR or 4 plex you should definitely contact property management companies in the areas where you invest and have them help you rationalize the numbers.