Of course, their debts will also be used in the qualification process, so you'll need a cosigner with a very positive debt-to-income ratio.Regarding a property, don't pick one that's what YOU want, pick one that will make money.Guessing you plan to rent out the other bedrooms?

As far as which approach is better [for your], it depends on your overall financial situation, the amounts for the property and run the numbers, and what your plans are for that property and future properties.Putting a down payment large enough to avoid PMI can make a difference. 

We recently closed on a condo in Medford as our primary residence, which I am planning to rent out in two years.

Build in time buffers for city plan checks?

I plan to expand to the upstate as well though.

I live in one of the highest cost markets in the nation, and recently lost insurance coverage and now have the California FAIR plan (yay).

Do you have backup lenders lined up, or a plan B?

Answering your question requires some knowledge of your financial plan and what you would do next with the money. 

What do you plan on doing with the property/ what does it need? 

I am okay with doing this for free, my goal with finding someone to mentor me is to get a better insight in how everything works, and to work on my abilities and get feedback on my work from someone with more experience.The plan after i get my green card is to partner up with my friend who is working on getting his real estate licence, our plan long term is to start by flipping houses and then down the road get into either short term rental or long term rental.