There's a very specific ways to calculate FHA income, and it will be highly dependent on how the deal and your ownership is structured.

If you PM me, I can share our structure for this.

With your maintenance and construction background, you'll definitely have a leg up in creating value, whether you go with a smaller home or a multi-unit property.If you're exploring seller financing and deal structuring, connecting with experienced investors here in Chicago will be a game changer.

Check out Norada Capital with a simple no fees structure and 12-15% annual yield depending on how much you invest.  

Consider strategies like rental properties, BRRRR method, flipping for capital gains, multifamily properties, mobile home parks, Section 8 housing, geographic diversification, and building a team.

It's crucial to consult with a tax professional who understands the nuances of your situation to determine the most appropriate and cost-effective method for your tax filings.

I want to ensure that the structure of these investments I am working on correctly address key issues for investors. 

This means you essentially have to save buyers 3x(5k-10k) = $15k to $30k through negotiating, finding the best deals, adding value with your property management or contractor contacts, etc.Lawyers use flat fee, hourly, and contingency pay structures primarily. 

Do you have tips for structuring short-term leases that protect me as a landlord while accommodating their needs?

Quote from @Stuart Udis: ....But I set the goal of acquiring 50 doors in the next 3 years using the BRRRR method and will then be financially free...isn't that a scalable business :)We see the above type comments from not so experienced investors or business owners all the time being posted on BP.