But in a rooming house, they pay a much lower rent cost, and get the benefit of a professional cleaning crew doing common areas, kitchens and bathrooms, free high-speed Wi-Fi for their streaming devices, etc.

It's always a good idea to connect with local investors or real estate professionals who are active in the area to get firsthand insights.

We/I am a professional, and our fiduciary responsibility is to our clients. 

If you never done one before, it's best to use professionals called "Expeditors" usually architects, to do a walkthrough and see how to do it.

Should I get into contracting with a flipper or custoM home builder for 50k a year 1099 and start my own llc and be a “real estate professional” and learn the ins and outs while making less money at first,  or take a sales job 9-5 that makes 150k a year w2 and build up capital first. 

Readers should seek professional advice.

I do some popcorn, Rice Krispies, sleeping masks, ear plugs, toothbrush /toothpaste, etc. local partnerships: find restaurants you may be able to get a discount for sending guests over for.

Most professionals will recommend a separate LLC for every $1 million in assets but I don't think that's necessary.

Readers should seek professional advice.

Readers are advised to seek professional advice.