Exit strategy is sell in 5 years, increase rents as much as possible, and get into a bigger deal.

This is a pretty significant increase in salary for my family.

Minimal (though increasing the last few years) scumbag upsell.

Are recent pay stubs enough to prove the drastic increase or will they ask for another tax form?

I feel like the trick is to know what you want to invest in and then learn enough about it to make sure that you minimize risk while increasing your return. 

It is technically true that you won't see a mathematical "gain" for several months or even years depending on the situation, but a lower rate will immediately increase your cash flow each month which could be a good benefit.

Also note that if the property is being sold for a much higher amount than it has in the past (often if it hasn't sold for 20+ years), there is a good chance that on year two your taxes will increase substantially as the county records the new value.Insurance figure around $1,000/year for a $100k price, or around $1,500 for $200k.

With that said our deal was: we would buy the property increase value (we have been able to increase rents and the commercial space wasn't rented at the time, we are about to rent that out) and then refinance, the thought was we could get the initial cash out after increasing the value of the property and repeat (sound familiar) - after which we would be 50/50 partners on the property.To my question - since this is a commercial property, would it make sense and is there value in converting this to a condo, where we could get more favorable terms on the residential units (30-year mortgages and 20% DP) versus the terms we have right now?

SDIRA qualified plans increase earnings for many by 50%.

The BP one really only works for single family as it doesn't take into account rent increases.