I think you'll find it's easier than you're initially thinking.

The downside will be I will not be able to pull initial investment out for five years and my IRA deposit will not lower my AGI (if I am over income limits).Any additional input?

Focus on making these initial images compelling and representative of the property's best features.

My initial thoughts, which are definitely open to change, are to buy a quad that I can flip into something around 20+ units with some investors and build off that with a goal of at least 60 units trying to cashflow around $6K per month.

However, we do have the flexibility to rent it out.Our goal is to refinance the property, as we initially purchased it with an interest-only mortgage, and get it rent-ready.

(after pay off, and cover insurance and taxes, profit of $1100 per month).Problems: We initially were trying to get properties paid off in 15 years or less so we would have profits every month in a short period of time.

One thing we learned was that if you have a "builder hat" on during the initial stages, our site plan may end up differently than if we had our "entitlement & permitting hat" on. 

So I just saw this post about Section 8 HUD tenants, and this post stated something along the lines of section 8 tenants being more likely to damage properties because they're section 8 low income tenants, and also something about investors not wanting to put money needed into Section 8 properties because they think they're just going to be ruined by these Section 8 tenants, and as someone who knows the entire process with investors, owners, contractors, tenants, and prospective tenants, this is what I have to say about it:In my experience, Section 8 HUD tenants are actually better custodians of the property because of many factors, but 3 of the main reasons being, there is an annual HUD inspection that is performed on each property, so this gives the owner an extra 'protection vector' against damages, also, the initial placement of a Section 8 HUD tenant requires a passing HUD inspection, therefore there's a record of the property's initial state prior to move in, and additionally, they want to have an easy renewal voucher process annually, and their unit remaining in good condition is an incentive for those reasons, therefore they are LESS likely to damage a property - their future depends on it!

Initially, we bought the larger house 7 years ago because we had family members living with us at the time.

The income might not be high enough to offset the initial cost, management, and turnover.