@Kevin Taylor I looked into Georgetown's real estate masters program (which can be done completely online - a bonus for me) but ultimately decided the time spent doing that program would be better spent continuing to work on my own real estate business, for reasons stated above.

It's now there forever and feel that when I move out either a future tenant or an airbnb guest(unit #1) would see it as a huge bonus.

If the property condition will qualify for a traditional mortgage (non renovation loan), and you can afford the rehab with your own money, then after you close on the purchase maybe consider getting multiple credit cards with HUGE sign up bonuses/points, use the cards to pay for the rehab, pay off the cards each month, and enjoy the nice cash back or travel point bonuses. 

Personally, I get a bonus when I sell a property so I have a chance to make extra money every month or two.That works for me.

It also has several other benefits (bonus depreciation, reduction of tax payment on the deferred gain you invest in the OZ by 10% as per the 2021 regulations, and tax free returns after 10 years). 

You were generous with your expenses, which is a good thing.

Most long term buy-and-hold rental investors treat appreciation as a bonus and never factor it into whether a property is a good buy.As I said, this is a bad rental.

I have a 2500 sq ft 3 bed 2 bath 2 living 1 dining and one bonus room rental.

You don’t need an entity to use sec 179.However, there are income limitations, business use limitation on auto, and potentially deduction limitation on auto deductions based on type of auto.If sec 179 doesn’t work, you can also use bonus but it has its own threshold and requirements. 

What should I do: studio, 1bed, or 1bed with bonus room (possible home office)?