The cashflow was good, but starting out with negative equity wasn’t ideal.

It will need Cap-Ex sooner or later, so BRRRR would be the ideal approach here; I'm approved for a conventional loan, but could start applying in earnest for a bank loan, or possibly pursue an option I have to partner up to make a cash offer (this deal is right around that 100k mark where my lender would only reluctantly do such a small conventional loan...another reason BRRRR is appealing).

Being out of state bring a whole another level of complexity, my advice would be to find a house in a B area in Detroit or in the suburbs, ideally with only cosmetics repairs needed (you don't want to open the walls on a house built in the 30's), find a good property manager, put a good debt in place and repeat the process. 

Seems like an ideal island car.

Although still not ideal, I think a 5% COC and 9.7% ROI isn't bad as I do still have upside potential in the rent amounts. 

It is certainly dependent upon the type of RE investment you are doing, but buy/hold in an IRA is less than ideal in my opinion.

I have some renovation experience so I was looking at doing some version of a live-in flip for a year (to take advantage of primary residence mortgages), move out and start renting the property, buy a new property, and repeat for 3 years - ideally with 3 cash flowing rental properties when I leave.I have a home I'm looking at that my relator thinks we can get for $180,000 and based on similar listings can rent for around $1400/month...its a new-ish build so it won't need a ton of reno other than a few cosmetic upgrades (<$5,000).

Select the one the has the most investment experience and connections (Ideally, they should be actively investing). 

That will be ideal, I heard someone create one LLC for each property.The problem is in CA, each LLC cost $800 per year, and accountant will charge at lease that amount per LLC.

E.