We have many questions about how to proceed, but wanted to start with this one:We are about to lose our current health insurance and are looking for a new plan.

I wish I could afford a new one...

Here's something that may be of interest. http://happyplace.someecards.com/rent/heres-the-hourly-wage-youd-need-to-afford-a-2bedroom-rental-in-every-state/

We want to buy a bigger house (with parking) but we need to sell our house first in order to afford the downpayment on the next house.

Yeah they have a financial drag, but nothing we can't afford.

Plus, I'm just not thrilled about forking out 20% when I would rather put that money to work for me elsewhere and opt for a 5-10 percent down payment.So in the simplest terms, if one uses math and logic, we clearly have the means to afford the house, but with traditional financing, the 20 percent will be a bit of a stretch for us.  

She has health issues and says she want to get this done.

We offer financing for all credit types, affordable down payments, and will work hard to find a way to make this house your new home.If you want a quiet, peaceful living experience for your family, This is definitely the place you want to be.

Starting out I would buy the nicest 4 family that I could afford in an area that I wanted to live in.

Disclaimer -- I'm paying debt off right now deferring an emergency fund and relying on a contract job that could go away tomorrow; however, my wife makes enough that we can afford our three properties if I'm not working.