However, there is this quirky rule that applies only to 3&4 unit properties - it must pass the self-sufficiency test.

This is precisely where I am at in Dayton.I need to get to Dayton Soon to facilitate the claim on my recent fire loss so that would be a good time to meet the good people at the VA.I don't have sufficient resources to make a new non profit venture workable yet but that is an idea I am exploring.

With two houses, spreadsheets and a couple of directory (folder) hierarchies on your computer (one per house) should be sufficient to manage things.However, if you are planning to grow, an accounting package (that allows you to create departments and/or cost centres), perhaps coupled with a simple CRM would check off most, if not all, your boxes going forward.

With a mid Fico score of 580, you should be able to obtain FHA financing as long as you have sufficient income and debt ratios meet underwriting guidelines.

@Marshall Leipprandt touched on a good point about the VA entitlement that can be a roadblock.If the ‘buyer’ assuming the VA loan is a veteran and has sufficient remaining VA entitlement, they can ‘swap out’ to use their VA entitlement to free up the seller’s entitlement.If the ‘buyer’ is not a qualifying veteran, the seller’s VA entitlement stays tied up in the existing mortgage until the home is sold or the mortgage is paid off.

For example, you are going to pay a premium for lake-front or size-able acreage, are you able to pass that along for a sufficient ROI? 

You should have enough equity that you could take out a mortgage sufficient to pay the siblings off and you keep the property.

On that same token, we aren't subject to the ups and downs of the market other places experience either!

Work with your CPA to figure out a reasonable salary dividend split, but make sure it's not just a token dollar amount cause that is ridiculous and a red flag.However, it's worth noting that the 1099 thing isn't directly related to real estate professional status.

When I started my average deal size was $250,000, now it’s $2 million.I believe that with your background and motivation, spending two or three years with a successful syndicator as an employee or associate will be sufficient to enable you to open your own syndication business.