To mitigate this, I've devised a plan that involves leveraging my primary residence.I've been residing in my current home for the past five years, which I secured at a very favorable interest rate.

Planning to occupy one of the units and use the other one as STR.

The process can be started about a month prior planning for a 30 day close. 

Talk to her and find out what her plan is, but remind her you need to get paid.

it's possible but unlikely. a great CPA who specializes in REI will be able to help you plan AHEAD for tax time and use different pieces of the tax code to your advantage, based on your unique situation, and ultimately save you way more in the long run. would you rather pay $750 to have a return done & get a $5,000 return, or pay $30 to have a return done and owe $5,000?

Check with your company’s plan.

I mainly plan to flip and hold rentals, but I ll also be wholesaling whatever deals don't work for me or I can't close on.

My STR is a lake house so I have a 2 page liability waiver that I have them sign if they plan to use firepit, dock, or canoe/kayak.

Also Currently taking the NH RE license course with plans to go with Keller Williams.

It also depends on your level of tolerance, are you planning to self-manage or would you be looking to hire a property manager?