Does anyone have any experience with Pillario Property Management?

This is a common issue, but having stricter cost control measures or a contingency buffer in place could help on future projects.

I'd focus more on the market. if you are looking for new builds that cash flow I'd look at markets with low cost of construction in the midwest that also have good market drivers.

I'm exploring different funding solutions to understand how others manage these situations.

You can also look at the home for the ARV potential.For example how much will it cost to renovate versus the ARV in 6-12 months to then use the equity doing a cash out refinance to buy another property.

I'm wondering if cost seg can still be done just without taking the added bonus depreciation - it seems that perhaps it can. 

My 2 cents, Save more for the downpayment, closing costs and reserves.

Calculating the Deduction: Choose between the simplified method (a flat rate per square foot) or the regular method (actual expenses).How do you manage your home office deductions?

I’m new to real estate but have a background in project management. 

The other "economical" areas are going to be more management heavy (think cheaper houses that are expensive in the long run) and the A/A+ neighborhoods will be very difficult to get cash flow (think Elmwood Village or Hertel Ave duplexes that are $350-400K but gross $3600/mo on the top end).