., we use QuickBooks Online exclusively for all of our REI Clients.

@Caleb Webb You're past the point to qualify and exclude any tax using the primary residence exclusion.

I'd tell them about the CFD and expect it to appear as an exception on the policy but even if you don't, there's an exclusion in the policy for matters you know about that the company doesn't. 

They also tend to not care as much about the time because they are trying to hit the 2-year mark so they get the capital gains exclusion when they sell.

Aside from any state-wide laws, you're actually investing exclusively in blue locations.

For example, if you rented for 25 years and then lived in it for 2 years, the capital gain exclusion you’ll be eligible for is 2/25 of your gain.

If the seller does not accept, then I give them the option to not take my counter offer.If I paid the "non-refundable" deposit and the seller walks, then I am out the money.

If you are very experienced, working with the listing agent can give you an edge in getting your offere accepted, but if you are not you really need someone on your side.Looking at your numbers, have you spoken with a lender yet.

The unit that is not updated, I've already done significant upgrades like flooring, new trim, doors, appliances and current tenant accepted my increase to $850/MO.

Hey gang, big update from my end- just had my offer accepted on a 4-BR SFH in Madison proper!