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.

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.

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

The BRRRR project is a short term rental in Maine, and the sale falling through meant that the timing would not work out to get this new property up to catch the busy season.

Just the brewery.What if your distribution plan doesn’t work out?