Sell My Primary for a Larger House Hack in an Expensive Area?

[Nico Dandini]

I live in an expensive area. Specifically, I'm house hacking a 2bed/1bath condo (living in one bedroom and renting out the other). I don't have enough cash to purchase a house hack without selling my condo. I have about $10K in savings, and if I sell my condo, I'll net about $30-40K. Average price for a SMF in this area is $500-600K. 

The part that scares me the most is if I sell my condo and my offer on a new SMF doesn't get accepted, I could be in limbo. Not to mention, not sure what I would do with my roommate if things didn't pan out. Also, if I do get a SMF, I won't be able to pay the mortgage on my own. I'd have to rely on tenants because I don't make enough to cover the mortgage on a SMF in this area.

My question is, would you take the chance of selling your primary to have enough funds to [hopefully] get an offer accepted and buy another property? 

[Nico Dandini]

@Marc Starkman I've thought of keeping my condo and investing out-of-state, but I'd have to save more money before I can do that. I figured selling the condo, putting down 3.5%, and house hacking in my local area would be the next fastest step. I guess what I really want to know if the thought process above sounds like a dumb or too risky move.