For example, should we focus on acquiring one high-quality property in a strong market, or would it make more sense to spread the investment across multiple lower-cost units in emerging areas?

I have tried to get quotes for these properties and I haven't found a company that is willing to insure me because I have open claims.

My father did this in Portland on two properties, for elderly people I think. 

Hi David, you need a discounted propety, have you tried hyper focusing on off-market properties in your desired area.  

I just DM’ed you but I’ve househacked a handful of properties on the northwest side of Chicago.

Quote from @Enrique Toledo-Perez: I'm a Realtor and I'm wanting to get into fix and flips by working with wholesalers and buying properties in neighborhoods with a good spread.

Be able to get into my first, 2nd or 3rd property?

Many months of costly vacancy, local market rent & resale deteriation, special assessments, property taxes and maintanance fees suggest a quick sale would have been the wise thing to do 2 years ago.

@Travis Boyd, 19 of my MTRs are in multifamily properties.

I think a better option is to get a job in property management.