@Luke NaylorThere is some high powered PM software out there, but those are typically not a good fit for buy and hold investors with your size portfolio.

Note; these are all photos of properties in my company's rental portfolio.

Should I use a portfolio lender?

I have used this myself and would highly recommend this as you build your portfolio.

We may avoid the whole thing and go with a portfolio bank. 

Im now heavy in the learning and evolving phase listening to all the podcasts everyday and “cash flow quadrant” in hopes to sytemize better and scale up my rental portfolio. Ive

Yes, when economy sinks - the rents will go down, the vacancies go up etcBut you will buy more rentals with less money and they will give you the returns as well.You're overthinking this, man.....just do something and you'll see how it's working.It's not like you're investing all your money in one business: keep working, build your portfolio and then you'll see more opportunities. 

I am trying to build up my team to start buying investment properties, both house flipping and to build a portfolio.

I have the occasional one that leaves after 1 year but if your goal is to buy rentals then the more you get the placement fee will become less critical as the whole portfolio will average out most tenants staying for multiple years. 

Small banks in my area give the best "in house/portfolio" loans.