@Brian Gerlach great tips Brian.

Any tips for closing the first deal?

Do it in a spreadsheet rather than online or an app, the process of completing it by hand is meditative & encourages one to think and focus.

I wish we could both qualify for FHA financing at once but the hubby who's a CPA just switched accounting firms last October so he wouldn't qualify without the 2 years of employment at the same company and my income alone probably wouldn't be enough to qualify me to purchase either property by myself, since a big chunk of my income comes from tips and self-employed side hustles.  

Some helpful tips on how to think through a strategy and take the first steps would be awesome!

Any other gotchas and tips that you can think off worth sharing?

Other than using cash app that puts a cap on how much you can send/receive within a time frame.

Is there a way to shelter them from the tax burden and how should I go about this any tips? 

I use an app called ICBA in order to pull up local community banks (often portfolio lenders) that can be flexible on down payment requirements and lending terms.

I would greatly appreciate any help and tips that anyone may provide.