One lesson learned is to incentivize contractors to adhere to their promised timetables.

I think it’s doable with this current time table but how about next year when my goal will be 12.My questions are:1.

As long as you have a time table to reach your freedom numbers then its like any job trading time for money..

Need to do a more detailed analysis here but I would expect relatively low cap-ex in the next 10 years.Home is in a good area (on a quiet street but still walkable to restaurants/bars/parks, schools are average to above average)Expected rent would be about $1500/m based on quick analysis of current listingsOur new location we're moving to will be about 10-15 mins awayI would like to manage this property myself but budget for property mgmt anywayIf I get into this and HATE being a landlord, or decide owning rentals isn't right for me, I have 2 years to figure that out and at that time could still sell the home and not pay any LTCG tax on the proceedsShort term goal: Since my personal situation will inhibit my time and ability to pursue scaling a rental property business in the short term (say 5-10 years), the goal of renting this property out will be to pay it off as quickly as possible and let it sit there providing good monthly cash flow, or possibly refi to lower monthly payment and increase cash flow if the payoff timetable isn't short enough.Long term goal: I would tentatively like to scale into owning maybe 10 or so rental properties at my time of retirement (say 20 years from now) to provide good cash flow in early retirement, and to keep me busy.

Do you think construction will work it's way up there and if so, what's your estimated time table?

That sounds reasonable to me, but be sure to have that written out in your budget for this property, as well as your timetable for when you are able to acquire your next property.

My time table was 14 years as that was when I would be looking at retiring.  

Everyone is in a panic about their flips or their real estate business, but we do not have a timetable for when the shelter-in-place orders will be lifted in each area to even assess how much we should worry.

Im an investor in Chicago and I’m looking to get into my first real estate deal within a 2 year time table.

This is not a predictable event with a predictable time table or set of outcomes.