You can't escape Healthcare and Taxes

[Anthony R.]

So I'm in the final stages of living 100% off of my rentals. As I prepare to take the final steps (probably in the next 12 months or less) I'm trying to answer a couple nagging questions I have.  

First, is there any tax surprises when leaving a W2 job for rental income? Currently my rental income makes up about 75% of my annual take home and it has been increasing to that point from 0% over the last 5 years. I have a CPA do my taxes each year so assuming he's not screwing me, I anticipate that it shouldn't change that much. However, I don't know and I'm curious what others have experienced. 

My second question is, what does everyone do for health insurance? I went from my parents health insurance plan, to the Army, to whatever plans my W2 jobs provided. I've never had to buy it in the private market so I'm not sure what to expect there.
(Just for me, no dependents, 31, extremely athletic, so I'll probably want something that can handle hospital visits) 

 

[Philip Williams]

Hey how's it going, the biggest problem with not having a w-2 income is not how much you will get taxed it's more so your ability to get loans. As i'm sure you know rentals are very friendly come tax time, your tax burden will probably be very small. On the flip side when you go to get financing for future rentals it's going to be very difficult. As far as health care I have had private insurance for my entire adult life since I've never had it through a job it is fairly expensive sadly but depending on your income you may qualify for subsidies that will help out some.