Ultimately I have determined that my LTR portfolio will continue to be my bread and butter but we may try to get a STR as a supplement.

Retirement: Pension, supplement for social security until age 62 (then social security), TSP (401k), Vanguard Roth IRA, Vanguard Brokerage account, and rental property income.

The questions that arise-When and why does supplemental taxes come into play? 

As long as the heat pump you choose can handle the coldest night you will encounter you can go with just a heat pump, otherwise you need some supplemental source of heat whether a gas furnace or an electric heat pack.

Adults learn best in person, and you can supplement with online, but that should not be primary.#2...Ask to see the training calendar...same thing...no calendar...then you have to question if it will happen and when.#3...Ask how much it costs...especially when you are new and perhaps don't have significant real estate revenue stream.#4...Ask their expectations of you?

You need to back it up with supplemental data from Airbnb/VRBO.

I am a buy and hold guy, I do not need the cash flow to supplement my income but I also don't want to lose money or have terrible returns.

I always feel no matter what you do, or what course you go with, you continue to use BP and the other valuable resources to supplement and continue your education.If you've not listened to podcasts (especially the Flipping Junkie podcast and the BP podcast ;)), you should definitely start there.  

Consider other ways to supplement your income while you build your REI business.

If she can provide a legitimately good reason for the bankruptcy and has documentation to supplement her reasoning she may be worth considering.