Once you go with a minimum 6 month lease your turnover costs, potential damage, make ready costs, repainting and repair costs, all go down dramatically.  

Do to the state mandates that require 100% reserves in all categories, combined with the rising cost of their neighborhood insurance policy, my strong recommendation is you find out what further anticipated spikes in association dues & if any possible special assessments are looming.

House hacking with an FHA loan is a great way to minimize living costs while building equity, or you could invest in an out-of-state rental for steady cash flow.

It cost me $8500 in my HCOL to get the electric separated on a 3 unit.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Streamlining Renovations for Efficiency & Cost ControlManaging multiple renovation projects at once demands an operational efficiency that can be tough to achieve.

Evaluate Property ConditionOlder Chicago buildings often have charm—but may come with hidden costs.

Does a cost seg or bonus depreciation actually help you in any way? 

I still have a full-time job, but my goal is to start with 1-2 flips/year for the first couple of years, then ramp up to 5+/year.Right now, I’m focused on learning as much as possible—market analysis, deal sourcing, estimating rehab costs, and raising capital.

Most PM software allows late fees to be charged.Ours allows us to absorb the cost of tenants paying electronically thru the software - it usually wants to charge tenants, but we want them to pay electronically.We manually charge tenants a Processing Fee for mailing in their rent, a slightly lower Processing Fee for depositing to our bank.Your success will depend on the Class of your tenants.