I am thinking I will start by targeting Arnold/Imperial and work out from there if necessary, probably west toward Murphy/High Ridge/House Springs before moving south.

It was crazy, and when a place with homeowners gets this intense it is not a place to go for investing in STRs even when there is no local regs. 

Even if you're not making much profit at the start because you're investing in a better area, it should work out fine.If you're losing $100-200 per month but have a stable job, you should be okay.Most people get rich with real estate through property value appreciation rather than cashflow.If you're comfortable living with roommates, you can purchase a house in a good area you like and rent out spare rooms.

My main issue with the current way your sales team is handling onboarding to Wealthability is that such a large amount of funds are being asked up-front without any hope of a refund if things do not work out and are not up to par. 

I tried self managing my first year, it didn't work out great as I rushed and rented to the first person I found.

It will work out better for him in the end because rent rates are increasing faster than social security income.

If you are married with kids like I was when I first started, it might not work out.

A renovation also allows you to build a great team, something you'd want work out before starting on a new build.

And so they can see it before anybody else can, unless ofcourse you go door to door or do intense research on your own to find good deals without real estate license.

You can definitely work out something with the seller that makes your offer contingent on the sale of your current apartment.