If for some reason it were to happen, there's a couple workarounds that can be done.

Meeting that 2 in 5 of the last requirement allows a single owner to shield $250k of appreciation and a married couple to shield $500k.Unless you predict a lot of income from the MTR or you feel that there is a lot of appreciation incoming over the next three years (minus time get the property sold), you may want to consider collecting your $100k (passing GO) and redeploying that money to whatever you feel is its best use. 

I have a couple of short term first trust deeds ready to mature and need to re-deploy this capital.

Under $150, easy to install and use, tenant can set their own code but landlord can retain the master and always have access, tenant can't lock themselves out, standard key for emergency backup, batteries last a couple years, etc.

We will not work with anyone who has not been to Milwaukee and spent at least a couple days with us, so we can get on the same page on asset and neighborhood quality. 

You learn the most about being an agent in the field and by choosing a good first brokerage with good training either in-person or online, depending on your preference.

Quote from @Taylor Robertson: I've been working with an agent for a couple months now in hopes of finding my second deal.

One already had electric heat in the upstairs unit and the other duplex needed a new boiler when we purchased it anyway, so we installed a new propane boiler for heat/hot water in the large unit and a couple Rinnais in the 1-bed unit.

I'd prefer to play it as safe as possible.

Appreciation is good in TX but I’m breaking even the first couple years when I buy here.