But I want to add some color on how I look at properties, regardless of house hack or straight investment:Would I live here with my wife and two small children?

Someday I'll be ready for this, and I can cut my teeth learning to be a landlord in the meantime.

When you put up an entire portfolio for sale, you're naturally cutting down your potential buyer pool to bigger investors.

@Kristen HernandezYes, get your license so you can keep your commission and cut out a selling agent.Have your marketing down or just hire someone good at marketing PPC or guerrilla.

Repairs should be straight cost.

Any ideas, thoughts, caveats, straight up warnings? 

(No realtor fees as I am able to sell privately)Am I able to use this to my advantage for my taxes to offset my 2019 income ($185 000 from my job).I’m wondering if it’s better to cut my losses now and to claim a loss, than to be out of pocket every month and wait it out.I also plan on purchasing a 4 plex cash flowing property very soon as well.Any help would be greatly appreciated.Thanks!

A lot of time the cut off for "short term" is 30 days.

Note: I'm not saying I would cut corners, do shoddy work or skip having work done by professionals, I am simply hoping to avoid government expense and red tape. 

If everyone likes it, I get my contractor to walk it and give me an SOW, then I'll throw it to a lender to make sure their numbers line up with mine.I HIGHLY recommend the BP calculators, they are the most straight forward and best I've seen.