I plan to stay in this general area for at least the next 20 years and think buying real estate would be a great way to diversify my investment portfolio.So in almost any scenario you will come ahead buying vs renting over twenty years probably well less than half of that, but the investment you are making is a long term investment you probably won’t be able to leave after a year or two and rent for more than your mortgage, I’d really think about where you want to live medium-long term, than any investment metric, because the longer you stay the better the investment looks, and if you can move out sooner great, but I’d guess at minimum you’d have to stay 5 years before rents would catch up to your mortgage. 

You've done a great job with keeping your debt low so I have no concerns about your level of discipline to use/reuse a line of credit.All the best!

Stay consistent, follow up relentlessly, and don’t get discouraged by setbacks. 

I used it for the first time with my most recent renter, secured through Furnished Finder, and when my renter decided to stay beyond the inital two-month lease,  Worry Fee Waiver asked specifically for a lease extension, not a new lease, indicating the switch to month-to-month. 

For example,  if no one else bids on the property or it stays on the market longer than the bid window and they do not accept an offer?

He didn't complain or ask any stupid questions during his stay and when he left he left behind 6 tiki torches and tons of OFF spray.

This time from "Suzy", who tells me she is the agent for a certain Lorrie Morgan, and Lorrie and her family were to be staying at the cabin. 

Contrators suck and you have to stay on them every day Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I have launched in markets and have been the unique high end stay.

I do hope we move and stay in San Diego long term (20+ years) like I have with Chicago (40 years).