We are personally comfortable being renters as it suits our frequent moves, but I can't help but feel like we could really optimize certain advantages like BAH, and VA/TSP loans with the right amount of research.The problem is we don't really have the time or interest to be long-distance landlords, and with very young children (and more on the way) the immediate time suck of rehabbing and the home chaos of living in a place under construction (if we went the BRRRR route) is almost completely out of the question. 

I sleep well at night with this strategy, but I can’t honestly say it’s not frustrating striking out so frequently.

Thought maybe I'd get a bite over here on the page I frequent.

We're frequent visitors to the Bay Area (dad went to Berkeley, sister/brother-in-law work in Silicon Valley) and know the area. 

While most houses probably do rent for what the list price actually was, it rarely goes above that but could frequently go below.

Department of Justice's publication Frequently Asked Questions about Service Animals and the ADA which are relevant to your situation:Q: Are service-animals-in-training considered service animals under the ADA?

I have a local property manager, but I still travel there frequently to do work on the homes myself.

She means well, but she is frequently paying late fees on late rent and I could not just send her a bill for $376.50 and expect her to be able pay it.I hope that adds some clarity to the situation.Thank you!

Other areas to look at would be near Siesta Key, Long Boat Key, etc... they are nice areas with frequent vacationers

This leads to frequent move-outs and escalating costs of ownership.  5% for maintenance and 5% for vacancy do not even come close to covering these costs.When companies are competing to see who can race to the bottom first (lowering prices and selling property cheaper and cheaper) they have to cut somewhere in order to make a profit.