I want to know what you guys think is a better option:1) In 2 months when the lease expires let it turn "month-to-month" status and then 2 months later start New Lease with New Rent from scratch.2) Write an Extension Amendum now for another year but specifying the first 2 extended months have same rent as before and New Rent will take effect after.

It could be a job lose, layoff, tenants not paying rent, extended vacancy, tenant damages, etc. 

The “15 years” only means an extension of the 5 year period prior to selling IF you couldn’t live there 2 of the years as primary within the 5 year original period, exercising this active military option THEN proceeding with a 1031 like- kind exchange.As for active military application - military extension of the capital gains exclusion applies for active-duty military members who are away from their property due to permanent change of station orders to extend the 60-month period up to an additional 10 years.

Don’t over extend yourself too much where people take advantage of you.

It’s also an early chance to show that they have a landlord who cares, which may dictate how they treat the place for the duration of their lease.

Hard money loans are basically loan sharks and unless you find an insanely good deal they will suck out your profits (also very risky if the carry cost period got extended due to a bad tenant, etc.)

You have a car loan at 4%, but prevailing rates are now 3%.....you can "refinance" your car loan to the prevailing interest rate and save 25% monthly interest.In real estate, you can refinance to a) lower your interest rate (like the car loan example above)b) take out a loan larger than the one being paid off ("cash out")c) extend the term of the loan (start a new 30-year loan for a residential house, or refinance a balloon payment, which is typical for commercial properties).Keep asking questions around here. 

It's been 50 days, we're supposed to close tomorrow and have already extended once by 23 days.

First internally within the IRS and then, if needed, in courts.That said, the law does not specify any particular minimum duration of leasing a property to establish that it was a rental property.

You mentioned the high vs. low rents, so you're already thinking in the right direction, extend it a bit further.