Since I am entering this field in the latter part of my life (63), I do not want 'long-term' investments as I am not interested in making millions, but having enough for the remainder of my life to 'Vive La Vida Loca'!

Quote from @Peter Firehock: Introduction:Well you've certainly put together a long and comprehensive analysis.   

The best part is the free CD is nothing more than a bunch of vague suggestions about how you can make all this money in real estate and vague bragging sessions about how he has been around so long and wants to give you all his knowledge before he croaks (paraphrased) Someday I will be completely immune to the crooks attempts at separating me from my hard earned money.

I would also weigh if you plan on staying in the home you are in now for a long time or move in the next 5 years.

Sometimes a 5-10 unit DSCR loan is solid terms, but I'm quoting 7.4% ish for 5+ unit, DSCR.

As far as the bedbug cost, I would consider how long you are willing to let the place sit empty. 

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

As long as the wholesaler is direct with the seller and the deal is real, go for it.

I’m exploring a few options and would love to hear your thoughts on each:Airbnb Rentals: Is short-term rental still a profitable and sustainable option given current regulations?

A 4-plex would be ideal and you could play around with doing 1 long-term, 1 mid-term, and 1 short-term, plus you, if it works on your area to upgrade your income.