In fact, we ended up paying a bookkeeper $450/month plus the $90 subscription to QB online to manage our relatively small portfolio.

This person failed to pay the taxes for 2023, so I bought the tax lien.   

You have to find a great deal , in a good area , find a great contractor  who can get things done fast and priced right  ,  you have to then find a great tenant who will pay the rent .  

He told me I qualified for a discount based on expected income and that while the policy was about $350/month with my discount I only pay about $99/month.

Section 8 pays "market rents" that are UP TO the amounts as posted on their sites as set for each county / zipcode by HUD.

Thank you, I've previously requested a copy of the new Rules & Regs, and now have also submitted the request stating I need them even if I need to order and pay for a whole resale disclosure package, although that shouldn't be required for a long-term owner who just wants the Rules & Regs 

That means you are paying money to have someone rent your investment property unless you can rent for another $1000.00.My first question would be what is your equity position on the home?

You pay absolutely NO points; the seller pays them all.

My main focus is really to reduce the number of closings (due to fees) and to pay the family member back for helping cover some previous work.

You’re probably cash flow negative on your current property and then have to pay rent in the new city.