I added two more dwellings with septic systems.

You'll want to have a clear system and rules for how folks are billed.

It requires research into each systems useful life and future value calculations.

Tax, bookkeeping, sorting receipts from a shoe box into a usable backup system, phone calls with questions, etc...[2] When will tax return be done--before due date or after due date.[3] Are there blackout times when question calls cannot be made.[4] Will you need to buy (pay for monthly) any software.Good Luck!

I have a very ambitious goal, and I will need to break it down step by step and acquire the necessary resources and foundational systems to be able to scale.

Our property manager has earned our complete trust, but we still set up our systems to favor us.

I would hesitate to do it if you have a boiler heating system. 

My suites are legal but some reason were not in their system.

We have 10 listings here on the island and have built the systems to run a portfolio of this size at a very high level.

Once done and if your the most qualified tenant then I would rent to you.Maybe you voluntarily offer to pay additional rent or animal fee to show you are not trying to game the system or at least offer to pay a higher security deposit which you would get back if you take care of the property.You are not being fair by assuming everyone is discriminating against you with no proof.