For all the postcards, letters, "ringless voicemail", SMS spam and virtual assistants I get calling me, I think I've had ONE real honest person call asking if I was selling, and even though I wasn't,  I talked to him like a normal person and gave some advice about cold calling.

The thought is I could keep the same good tenant instead of gambling on an unknown tenant, the tenant gets continuity to their business instead of finding a new place for likely similar rent, and I get to increase my NOI for sale or refinance purposes.

Personally I lived in Seattle now Hawaii and I saw the light... need cashflow to eat (although i do admit that appreciation will make you rich)It could appreciate but I consider that gambling.

But it’s a gamble and I’m willing to take on a little risk.

On the other hand if you're 99% confident in your tenant's ability to not overreact to minor issues and that they won't spam you, then by all means give them your personal number!

Or is it too big a gamble?

I know trying to time the market is generally poor advice and more gambling then investing, but I am hesitant to start investing in a Roth now when the market feels like it is approaching a peak.

They spam it like it crazy.

Some buyers are getting smarter about looking to see if permits were pulled and closed for work performed, but a lot aren't so it is a gamble at sale.

Report as spam/block on your phone and move on.