I could bring the HUD statements (showing ownership of the US properties), my US incorporation documents, my Canadian incorporation document (the Canadian company that owns my US business), information about the ownership of my house in Canada (to prove I have existing ties to Canada and no intent of relocating to the United States, etc.)I am a little apprehensive of this and i want to make sure that I do everything correctly so I will not have any problems in the future with crossing the US border.

I am in a seller's market, I am trying to figure out how to correct my position. 

As far as my goals, I would love to help an investor up that curb appeal while adding some investing tools to my toolbelt.  

I understand that your wife may be worried about failure, but any kind of investment comes with a chance of failure so the risks must be understood prior to jumping in and the fear must be overcome with the confidence of being successful.Since you're starting funds are $0, a HELOC can be a great tool for getting started, but ultimately you will need some kind of funds of your own because you must pay the HELOC each month during the flip.

I've been doing some research into renting/renovating in Baltimore City.  We were talking about renovating our basement ourselves (it is bare concrete currently) and so I thought I'd do some research. While I was read...

You need to be careful that you do it correctly in order to not violate any SEC regulations with regards to raising and pooling money.

If I am missing something please correct me.

As far as the meet ups you would be correct, I don’t believe any BiggerPockets backed ones are in the area but there is a local meet up of investors monthly https://www.reinvestorgroup.com.

There are multiple ways that the structure can be enhanced.You've brought up more topics than could possibly be done justice in a forum post....real estate investing is so broad, with an incredible array of tools and strategies - it sounds like you'd like to introduce your investors to so much at once.

they are both short term rentals, correct?