What are some things I need to be on the lookout for tax wise?

If the investor chooses wisely, they can also access sponsors that have years more experience than they could ever obtain on their own.

If you are renovating, it is always wise to add 10 to 15% for unexpected issues that you may encounter.

I know many docs who live in Kailua and their commute time is the same as mine although miles-wise they are much farther.

Thank you @James Wise!

On a realistic note, how can you ever hope to catch up to or surpass a full timer knowledge wise and business wise while only having 1 foot in the door and not putting in as much time and effort as them?  

@James Wise@Russell Brazil@David NaccoThank you all for your responses!

These are some of the benefits of working our rear ends off for decades and saving, contributing to 401Ks and Roth IRAs, and investing wisely in total stock market index funds for years.You asked, "...can you qualify for more than one mortgage? 

You can't do that on an older home in the right Market, I can do 15% on an older home long-term wise if the home was purchased with good real estate acquisition techniques

You were paying credit card fees, towels and coffee and other supplies, higher insurance rates, self-employment tax, furnishing, high maintenance, decreasing Market saturation, booking site commissions, a lot of other stuff. third, 30 to 35 thousand on a $275,000 house is peanuts 'str wise.