Average stay - you’ll want to see how long the average stay is.

The payoff is worth it in the long run with reliable, on-time rent payments and tenants who are more likely to stay long-term, and take care of your property. 

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. 

I'd be very surprised if they would consider a less than total deal, unless they're really desperate.

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. 

Although the list may seem intensive, I look at it like this: The total cost of all these items can be much lower than the cost to repair a hidden surprise after purchasing a property to flip. 

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

For example, say it were a 2bd/1ba property, I would just list it for 1 nurse to stay and I would hit my cash flow goal.

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?

As another poster mentioned rates are lower than they've been in the previous 18+ months but unless some very surprising economic data comes out between now and when you did your refi it seems unlikely that rates are going up in the short term and there is at least a decent chance that rates drop a little more before then.