We as the lender are tasked with estimating countless figures for customers even though the lender has very little control over most of the figures. 

I would even suggest a Primary home or Vacation home to pull the cash out of versus trying to find a lender who will agree to be in 2nd lien position behind a investment property.

He needed to close in three weeks and didn’t want to deal with showings, contingencies, or the back-and-forth of working with a realtor.At first, we even suggested he list with an agent since he’d likely make more money.

@Sean Graham isn’t your example paying for another cost segregation, which will cost more than a 1031, just to break even on taxes?

I've seen some people house hack a single family home by renting out the rooms, but keep in mind that traditional lenders would not be able to use the income from renting out the rooms (known as boarder income) towards additional income on the application.

No effort to give his investors even 50% of our capital back.

Purchase price: $2,500 Cash invested: $5,000 Single family House (2 stories), 3 bedrooms, 1 bath. 1100 sq ft. on Corner LotSingle car garage with 16' x 24' lean too.

A landlord policy can be a commercial policy or a personal lines policy.It's the same as asking if you should buy a single family rental or a 1 unit building.Focus on the coverages and disregard the name of the policy.

For my first investment, I'm looking for a safer investment with a goal to at least break even in 12 months and possibly focus on learning long term cash flow and appreciation.

This seems risky, since I have to pay for repairs on a property that’s not even mine yet.