My next question is a simple one: through circumstance, we will almost certainly have real estate holdings in two states (Georgia and likely Pennsylvania).

Also, in the rental agreement, it says:"HOLD HARMLESS AND INDEMNITY: OWNER of rental property shall not be liable forany damages and/or injury to TENANT and/or their guest(s), or their personal propertydue to TENANT’S acts, actions or neglect.

I have seen some sellers wait two years to close on a property those are definitely rare circumstances.

What you are describing is a fully thought out partnership or pre-arranged circumstance.

This could bring real estate dealer status into the equation under some circumstances.

I do not accept personal checks under any circumstances for these move-in funds.This agreement is between_________________________________________, hereafter referred to as “Prospective Tenant(s),” and ____________________________, hereafter referred to as “Landlord.”Landlord acknowledges receipt of payment in the amount of $___________ from Prospective Tenant(s) as a non-refundable binder for the property listed above.

If a maintenance issue is due to tenant neglect or abuse, they should pay the bill.

As I mentioned previously to Hattie, I want to see what is realistic given my circumstances and what things to focus on at this point in my journey.  

If you hit the two-year mark before selling, you should be eligible for the exclusion.If you don’t meet the two-year requirement, you could look into partial exclusion for certain circumstances, such as job relocation or health reasons.

Facts and Circumstances Test: Based on all of the facts and circumstances, the individual participates in the activity on a regular, continuous, and substantial basis during the tax year.