(Also look into the FHA 203K loan)Another benefit to going with a multifamily is that it can "boost" your purchase price using 75% of the other income to help your debt to income ratio... so $1000 rental is worth $750 to offset any PITI payments.

I've been leaning towards a condo as I feel it would be way less maintenance and just less of a headache being this far away, as well as cash flow being my main goal!

I think a duplex or small multi-family would be a great way to start off due to the benefits you had mentioned, as well as the smaller down payment.

it's my understanding that you would still get the capital gains benefit, since you would have lived in it 2 of the last 5 years. 

Also many times it seems that a later HELOC is from the same deed holder or there is a 3%loan recorded on the same date as the 'main' loan from the same lender.

My Spouse & I are both dual military so If im right, there might be a slight benefit there. 

Box; rent can only be paid by deposit.For your convenience, the nearest location to your home is 123 Main Street, City, or you can execute a bank-to-bank transfer using the routing number provided.If you have any questions, concerns or maintenance issues, you may call or text my cell phone at <Google voicemail>, or you may email me at the address listed at the top of this notice.Please don’t hesitate to contact me with any questions about this transition or any other pertinent issue.Sincerely,<you, the PM>

If so, what have been the benefits to having this type of business model as an investor?

However, if you read them and if it covers your main concerns, it should be fine.

One of the main requirements of a HELOC is you need to own the house.