However your situation becomes a trickier case study since these properties first served as your primary residence which could provide additional benefits form a tax perspective not available to an owner of investment real estate and nobody has a crystal ball and knows the property with certainty will transition into an investment property. 

Overall, I'd do it again, in the exact situations already mentioned above by other posters.

There are financing options for self-employed borrowers in these sorts of situations, but they require a higher down payment than FHA.

Our financial advisor said it would be ideal if she does the apprentice type work with an experienced broker so we can learn the ropes.

**Faster Turnaround**: Brokers can usually provide a BOV/BPO more quickly than the time it takes to get a full appraisal, which can be useful in time-sensitive situations[1][2][3].3.

This works in certain situations as does a 1031.  

Or, do you want to have a situation where the tenants are complaining about the lack of AC?

Yale, in particular, has more money than some small countries, so they certainly have the financial means to invest in the city.

In this situation I would have personally provided these tenants with a rent deduction.

Consulting with an independent insurance agent can also provide personalized recommendations based on your situation.