You get renters that just like houses are much tougher on the units.How much land is this sitting on?

Though it's tougher to rent in fall/winter, if the place is only renting between 25-50% of market, I'd be shocked if you couldn't do far better than what they're paying you now. 

If you can NOT quickly get someone wanting the place in a few days, it will BE THREE MONTHs as after first of Labor Day it will be tougher to rent out to. 

I could HI Kevin,This transition that you're asking about above is extremely important to transition smoothly and plan for because it will ensure your subsequent VA use for additonal purchases.Once the current property is refinanced with a non VA loan this will free up your entitlement for additional use.The max conv limit in Ventura county Ca is 672,750 and the max loan limits for a high balance loan can go up to 95%.So what this means is theoretically you could refinance up to 672,750 loan amount with an appraisal as low as 708,158 dollars or higher before your loan is subject to jumbo/non conventional guidelines (much tougher to qualify for and has lower LTV's).The VA loan has some key features that other loans dont have:- a trade off of no monthly PMI but the upfront PMI is huge, equivalent to 2.15 - 3.30 Points (borderline hard money points).

Trouble will come in the form of units that are tougher to rent because they are difficult to get in and out of, as well as more damage from drivers that lack the skill to maneuver into the units in BOTH buildings

You are correct, in the 1st two counties, we are flooded with investors and prices are rising;  Competition is high and it's getting tougher and tougher to get a good deal.

I don't know where you plan on investing, but if it's out of state, it's going to be even tougher to pull off.

@Jesse BurnsThank you for that...greatly appreciated...being new to the area makes it tougher sometimes

While my area/market is different from yours, I'm sure not that much since it's not California or New York where it's much tougher to find cash flowing properties for cheap.

Tenants are often tougher on rentals, ESPECIALLY if they have kids.