Downside to this is adjustable rates with balloon payments on shorter terms.  

Are there banks that will do LTV in a shorter seasoning period (3 to 6 months).

The Medium-term plan would be to fix up my main building first while renting out the smaller building on a shorter-term lease.

If it’s positive $150/mo or negative $150/mo shouldn’t be a deal breaker. 3) in a few years when you’ve raised rents you’ll be cash flow positive on the shorter loan.  

Many agents would be happy to sign a sales agreement for a shorter duration.  

Then you should certainly make yours shorter term and make sure to make your note default if they default on the first, even if yours is current.

Good contractors are always busy , material prices remain the same in the winter , employees still get paid the same hourly wage , the days are shorter , and the working conditions are worse .

But since there is a limit to how much money the bank has access to....their rate will be higher...and usually a shorter term.

I am working on a shorter timeline like I mentioned, my lease is up August 01 2020, so I am not sure if it is even a realistic goal right now. 

But since there is a limit to how much money the bank has access to....their rate will be higher...and usually a shorter term.