Timing being one of the most challenging - you'd have to sell all five properties, and buy any replacement properties, within the time limits specified for a 1031. 

Consider creative approaches such as an older home with rental potential on a larger parcel of land that enables you to build "your" portion of the home in the backyard for example.

However, it made my partner @Rico Nasol and I take a deeper look at our own personal liquidity and analyze the way we were thinking about approaching our first deals.   

I have a property that I am looking to purchase, and I would like the community to tell me what they think.What: A fixer upper Duplex in Central California (buy and hold)Context: I attended a local REI meetup a few weeks ago, and was approached to purchase a property from a local Real Estate agent and Investor.

My approach would be to buy the one and feel out the situation. 

Entrepreneurship is exciting and challenging and requires a strong mindset which is what I'm discovering.

In general we like to take a measured approach that breaks up the DD into 4 areas: financials, initial walkthrough, compliance, and paid inspections/services. 

I own a number of rentals in places I wouldn't prefer to live myself, but I do have tenants that pay the rent on time, and are content to live there.I fully agree with her approach to your question, though... in order for anybody to give a good answer, one must first understand your goals.  

Finding off market deals is a little more challenging than looking on MLS, but it can be done.

Also, older mobile homes are very challenging to finance which makes them more difficult to sell.