This seems like the most feasible option, but it also seems like prices and rates are going to continue upward in that span.I’m not at all attracted to the idea of a wholesale operation, but perhaps that would be the way to get started?

It teaches you how to generate your own leads online though - not rely on 3rd parties. 

I can't speak for KC, but they're operating here in Ohio without a license.

I am striving to remaining in compliance with company policy, HUD, and the CFPB, although the goal would be to eventually replace my current income so there would never be any issues operating in grey areas.

We have always operated under the belief that "because we (the company) own the properties that we manage, then we are exempt from requiring a broker's license". 

Has a fully stocked operational liquor store and tv repair shop in the front, facing a road that gets good traffic.

That being said, for NYC that's not too bad and if you really can get a place that generates $3800/rent for $400K, that's a great deal.

I recently came into a windfall which I am looking to turn into generational wealth for my family as well as pay for my Mothers living expenses and younger siblings college.I've been interested in RE investing for a long time but never got too serious with it.

These safe harbor rules contain capital account bookkeeping guidelines that establish uniform procedures for recording the economic (not tax) results of partnership operations.

Most of the time the income generated by the building won’t even cover debt service.