@Brett Allen Crisp I'm also active duty, I'm also hundreds of miles away from some of my investment properties and I'm currently living in Jacksonville. So, with all that said, I'll give you my $.02 for what it's worth to you.
First, you're not doing as bad as you think. Just keep that in mind. By your own admission your property has cash flowed a little for the most part and your mortgage has almost always been paid by tenants. There are many landlords out there in a worse situation. Take a deep breath for just a moment and know that you've got something to be grateful for there.
OK, on to the meat and potatoes...property managers can make or break you. How good is your current management relationship? Do they call you to discuss issues before they act, do you have specific parameters set up with them so they don't spend over a certain amount without your permission unless it's an emergency, etc etc. Are you happy with the fee structure?
Remember, in Jacksonville there are lots of investors and lots of property managers. It never hurts to shop around for better terms if you're not happy. You can always re-negotiate your terms as well. Another thing to consider if you're in a position too; negotiate a lower fee if you let them manage multiple properties for you then get a second rental in the Jacksonville area. I've done this with my rentals in Nebraska and I only pay a 6% management fee monthly. That's awesome compared to the average 10% fee most PM's charge.
Another strategy that I use is to maintain a home warranty on all of my investment properties. I pay a small monthly premium (less than the traditional 10% of rent for maintenance expenses) and if there's an issue reported by the tenants my management company knows that they call my home warranty company first. I pay a $150 deductible and if something needs fixed or replaced, it's done. No $1500 AC repairs, no $700 plumbing fixes, etc. Some will argue that paying a monthly premium for insurance isn't worth it but for a long-distance landlord of many years now, I swear by it. My maintenance and CAPEX numbers are lower than the traditional 10% each when I factor in my premiums and deductibles.
You can work with your management company to write their management contract to stipulate that they should call the warranty company for all repairs and if something isn't covered by the warranty, they have to get your permission before spending more than a set amount that you determine ahead of time with them. I actually had an instance early on where my management company didn't call my warranty company (or me) and they sent one of their maintenance contractors out to fix an issue. The bill was over $1,000. When I pointed out that the PM failed to execute the maintenance in accordance with our written contract, they ate the $1,000 because they knew it was their mistake.
I think that's enough about management at this point; lets talk about taxes. While trickier, there are some things you might be able to do in order to lower your properties taxes. You can petition to have your tax assessment reevaluated if you think you can justify why the current tax assessment is too high. Perhaps you know the property isn't in as good a condition inside or outside as the properties around you because the tenants have produced a significant amount of wear and tear. Perhaps there is another oddity that makes your property worth a little less than the surrounding properties. These are the kind of things that might lend you to ask for a lower assessment. In the grand scheme of things though, this may not be a decent return on investment in regards to your time and effort if you feel like the current tax assessment is a fair assessment for your property.
As for insurance, keep a good insurance policy on the property. Last thing you want is for the tenants to accidentally burn the house down and you aren't able to claim the damages because you tried to save a little money by getting cheap on the premium. It's not worth what little cash flow you may be able to generate to take that kind of risk in my opinion.
Lastly, rents...when was the last time you and your PM discussed market rents and when was the last time your property's rent was raised. A good PM should be assessing this every time there is a tenant turnover. The Jacksonville market is appreciating right now so it's logical to assume that you'll be able to improve the rent (assuming then property's condition supports it) in Feb of '17 when the current tenant rolls out.
Man, sorry about the novel. I hope that helps. Best of luck to you.
