If you take a shorter term approach such as flips/assignments, you're also able to reduce your risk and exposure. 

We listed our first property on both Airbnb & VRBO to get maximum exposure. 

Real estate folks are learning a current work around by selling and in the same year buying another property and using the bonus depreciation (from a cost segregation study) in order to offset the capital gains on the sale.”

Therefore able to leverage scale and buying power across projects. 2) you get bids as you described and divide up the equity based on how much work they have into it. 3) to incentivize quality you must reserve equity of the profits for a bonus pool.

Property Management to collect rent, leases and etc would be an added bonus. 

You can always offer up some kind of bonus for changing their reservation.

What are some expenses that I should factor in for: capital expenses, insurance, bonus taxes, ect.

New everything and adding a second bathroom really helps with a bonus room that could be used as a second office or workout room.

I have side hustles that pay an extra 15k per year as well as a 10% annual bonus will be distributed in 2023.

I put a brand new kitchen/ 2 brand new bathrooms/ garage door on/ tons of other random odds and ends, all paid for from bonuses from work.