Feeling overwhelmed and slightly defeated starting out

[Josh Hackett]

Hey everyone!

I'm hoping there are a couple people that are in my position or that have advice on moving forward. I have been self employed for most of my adult life. I make in the six figures right now, but taxes have always been an issue when it comes to borrowing. I bought a condo 3 years ago and have around $80K equity after all the closing costs. I'm looking to purchase an investment property and have around $100K liquid to use, as well as the equity in my current residence. IF I don't sell my condo, it will rent extremely easy and passes the 1% rule with flying colors. But living here has made me realize how cheap it's constructed, and how much I HATE the ridiculous HOA that goes up around 10% a year for some magical reasons.

My girlfriend isn't happy living here due to wanting more space, a yard, not having to go up 2 flights of stairs, etc. etc. and wants to buy a "forever" home asap, but is also opened to a house hack situation where we buy a fixer upper. Also, we are in the Portland Or. area so prices........suck. She has be pre qualed solo for just over $300K, I couldn't be on the application due to me owning a home already, and showing a very small amount of income in 2016 and now even smaller amount for 2017. Think sub $20k per year, this year is sub $10k in income. Which is great on one hand since I owe a very small amount of taxes, but sucks for financing. 

I was excited to get my taxes back and go directly to a lender with them to see my financing options. Well now my financing options seem to be zero with me showing so little in income. 

I guess I just don't know how the heck to proceed. I'm bipolar when it comes to selling my unit, one week I definitely want to sell and use the money to purchase a new home, the next week I feel stupid for even considering selling because I bought this property the right way and got a killer deal. Plus my initial thoughts for purchasing were strictly for a rental eventually, and I'm in a great A location next to so many things, and Portland has already started spreading out where I am and developing the area for huge growth. 

I feel like my best option is to continue saving until I have around $200K to purchase a property in cash. I just don't want to wait that long and am ready to start now. I just feel overwhelmed with picking the correct path and right direction to head. Sorry for the rant, I'm just hoping to get some out of the box ideas or to be called an idiot and to calm down :) Thanks in advance everyone!