Yes, you can file jointly if you or your spouse qualify as a Real Estate Professional (RE Pro) and share the benefits.To qualify as an RE Pro you must:1.

While not in TN specifically, I have assisted clients do as you have described: live in a property as a principal residence for 2 years, rent it out for 3 years, then sell.Based on the situation described, you would appear to be eligible for the MFJ joint exclusion on principle residence on your 90% share.However, in order to retain that ability, the house will very likely need to be sold (ie, sale closed, not just under contract) by the end of this month. 

If everyone is truly active, it is now a joint venture and you can have a local real estate attorney form an LLC for you (which is much less expensive).

I did it by househacking 2 multifamily and joint venturing on about 20 units of commercial multifamily.

You must work at least 750 hours per year in a qualified RE business.So most people who have high-earning W-2 jobs outside of real estate wouldn't qualify.But the unique thing about RE pro status is that even if you don’t qualify but your spouse does, you can both file jointly and claim the losses from your RE investments to offset your other active income together.

They delay fixing anything, will repair things that clearly need to be replaced, and are genuinely a headache.

Yes most definitely, however each person are able to acheive 10 maximum conventional loans, so if each properties are applied jointly, then you both would only have 10 active loans/properties instead of 20 loans (10 from each person) So you would want to strategize accordingly and see how you can acheive your maximum potentials and have multiple properties with your partner.

George Washington acquired a significant amount of land this way, and shortly after acquiring such created SYNDICATIONS (he later used JOINT STOCK COMPANIES when they came into existence) to raise the capital needed for development.  

Then you and sis start looking at the market to find properties that fit your joint goal, and dad looks at his portfolio to find the places he wants to sell to get the funds to arrive at the model. 

It’s a balancing act for them, and time will tell if this shift adds genuine value for hosts or just distracts from core issues that need fixing.What would make the most sense is if Airbnb uses Experiences to enhance the guest journey while still keeping the focus on the quality of the core stay.