I own 3 rental properties in Ontario self-managing 7 tenants. 

Have you ever owned a home, a self storage facility, a MHP?

Given your stage of life, this could be challenging but worthwhile if you’re confident in handling the stretch.Sell, and reinvest in cash-flow rentals: Using part of the equity to generate cash flow with out-of-state rentals could create a retirement income stream now while still capturing SoCal appreciation.

These self employed 2nd mtg's are typically based on alternative method of caluclation like profit and loss statements if you're self employed or the last 12 months of bank statement deposits using a formula to derive an income from these deposits (like 50% of all annual rolling 12 calendar month deposits X 50% /12 months = monthly income).

If you are self managing 1-2 properties, minimal softwares are needed IMO. 

For those who self manage, I wanted to share a great bank I've been using called Baselane.

I am currently moving through my first assignment of RPA escrow period and all of the seasoned people who shared their "assignment of agreement addendum" experiences and insight has given me the confidence to know I am moving in the right direction and taking the correct steps in order to close this transaction correctly. 

If you/your family have the time and the wherewithal than self managing could work great as well, just need to build your team. 

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?

After that, you'll be much more comfortable and have the confidence to take action when you find a good deal.