The emotional / confidence factor does matter when it comes to conviction to hold over the longhaul.4) Are you improving or decreasing in the quality of area you are going into in order to acheive this cashflow in PGH?

Thats how they know your properties condition has “improved”.

Hey Dave, since I have mortgages on these properties, would it make sense to bring cash to the exchange to cover the mortgage amount (or pay off the mortgage before doing the 1031) and improve the cash flow for the newly acquired property?

There's nothing left to cover expenses so you better have deep pockets to cover maintenance, admin, turns, etc.If you think you can quickly improve rents to a point that covers your expenses and pads your pocket a bit, then maybe, IF it hits your return threshold.If you're buying cash, then the mortgage is not a factor. 

FHA loans with low down payments are ideal for this.In the meantime, focus on improving your credit score and maintaining a solid financial foundation.

As insurance woes grow over the next couple of years, I dont see this improving. 

The IRS has said, since 2017, that the improvement ratio or $ value is what your taxes are assessed as, unless you have a really compelling reason to use a different value. 

A post on recapture:People are concerned about recapture when they cost segregate their improvements and for good reason.Recapture is real, and those deferred taxes will need to be paid.But fear not!

@Philip Jones we've helped our clients do over a hundred.As some of the lenders posting have pointed out, the challenges are:1) Property value and corresponding loan size2) Appraisals have much better comparables than 5 years ago, but may still be an issue.3) Property condition can be an issue via the appraisal4) Ownership seasoning - most lenders looking for 6+ months or incredible documentation for cost of improvements made.5) Most DSR lenders require professional property management.Always try a small local bank or credit union, but most will expect you to transfer your business bank accounts over to them. 

Its a great feeling to provide improved housing and providing jobs to other individuals who want to be their own boss.