Ann Arbor is a strong market so if you hold onto a home for 15 years you will easily have alot of equity to create a nest egg for your kids.

If you are looking to build your retirement nest-egg, I assume you are looking for long-term buy and hold opportunities.

I'm concerned about buying something I'll regret later, so I'm debating whether to try to find a new home now or possibly rent something while I continue my education/networking/start marketing and continue to save up my nest egg.  

@Chad Gray I hear you on getting a few lump sum payments to generate a nest egg.

I'm hesitant, because I want to reach a nice nest egg of about 5-7K to pay for down-payment, closing costs, and immediate unforeseen issues (i.e. job loss). 

I would recommend reading Rich Dad Poor Dad and start saving a nest egg.  

You take into account the income tax deduction for the deductible part of self­employment tax and the deduction for contributions to the plan made on your behalf when figuring net earnings.Earned income includes amounts received for services by self­employed members of rec­ognized religious sects opposed to social se­curity benefits who are exempt from self­em­ployment tax.If you have more than one business, but only one has a retirement plan, only the earned income from that business is considered for that plan.Also, the general purpose of  a solo 401k is to grow your nest egg; therefore, when a solo 401k is invested in real estate, all the earnings such as rental income and  proceeds from the sale will flow back into the 401(k) and grow tax-deferred in the case of pretax funds.

I just knew I want to have cash flow when I retired and hopefully provide a nest egg to my kids like my mom did for me.

Without knowing the details or analyzing the numbers selling this and flipping more will tend  to build you nest egg faster.

-Let sleeping dogs lie -Don't rock the boat -Don't poke bears-Never kick a hornet's nest!