Your insurance may also not cover you or your tenants. 

Her retirement income would be used to cover the mortgage.I hope this gives you an idea of my plan.

@Paw Nouri Maybe in your area they will cover damages but not in Maryland.

Not every state or city mandates that any landlord has to accept Section 8, because the landlord has to not only subject their property to Section 8 inspections, rules and regulations, they also often have to separately arrange for the tenant to pay the non-covered part of the rent and can face difficulty evicting just based on that.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

I would venture a guess that many investors believe that agents who cover the same territory are competitors, however as I'm sure you are aware that there is more success in collaboration as agents than competition.

Will the cash flow even be able to cover that?

I handle St Augustine/Ponte Vedra/Palm Coast but can certainly help with Jacksonville and based on your goals there may be other opportunities to explore.To cover off insurance from previous comments, the market has changed and it is competitive with new carriers entering the market. 

I have decided to look into a heloc, I'm a bit newer into realest state investing, I have completed a couple of fix%flips this year, I currently use hard money for the purchase with 10% down and I cover 100% of the rehab, with that said even just doing a couple of homes at a time, I find myself around 200k out of pocket, I think it would be a bit easier on myself and wife if we utilized a heloc vs just cash, my primary should appraise around 1.1m and my mortgage is 640k, I'm looking at pulling about 250k for a heloc, I don't want to refi the home and cash out as I only want to pay interest on funds as I use them ( I know I won't always be using the heloc cash) Any advice or even knowledge for people in a similar situation, and anyone have a referral for a Heloc?

Their guarantee to cover the mortgage if they don't rent the property is a red flag, too.