Awesome to hear you have a specific date picked out to take the test! 

Structuring your lease in this way would benefit you by 1) locking in a longer term contract to avoid turnover costs and vacancy loss; 2) it moves your lease end date out of the winter season and into spring/summer of 2026 so it can be more easily marketed and re-rented to match the seasonal demand cycle; and 3) it avoids any upset/angry tenants who may have been incorrectly assuming their rent was going to stay in the $1,200 range after their first 6-month lease term.Would love to hear any updates you have on how this one shakes out for you though!

So for example your American Express statement closing date is December 10 and your payment due date is January 4.

If you can rehab your way into a house-hack of a small multifamily and live on site, I think that would allow you to improve your cash flow by getting a short-term rental license even though the city is making it harder to do STRs.

I have seen many investors lose money due to purchasing site unseen.

Current lease term (expiration date, month-to-month)7.

All of the mortgage rate forecasts are probably a little dated and the next time they update the projections will go up. 

Proc. 2018-58 -SECTION 17.02(1)'s provision that "However, in no event may a postponement period extend beyond: (a) the due date (including extensions) of the taxpayer’s tax return for the year of the transfer."3.

Although for me being one a premier client of our title company they would do date downs for me for free and also keep a running spread sheet for me.

For something more robust, tools like Excel or online calculators from financial planning sites might better suit your needs.Your ROI Formula:ROI = (Net Cash Flow ÷ Total Out-of-Pocket Investment) × 100For your scenario:Net Cash Flow = Annual Rental Income - (Mortgage Payment + 401k Loan Payment + Other Expenses)Total Out-of-Pocket Investment = $40,000 cash + $50,000 loan payments over 5 years.I came across a piece in Bloomberg recently discussing creative financing, and they touched on ROI calculations for multiple loans.Personal anecdote: A buddy of mine leveraged a 401k loan for a fourplex.