I'm curious, at what point does this reflect poorly on PM and suggest I should get antoher PM?

Funny enough, I was going to suggest you move out of SF due to the high cost ;-) I'd suggest going down the SF condo route to start as financing for commercial units is a lot more difficult than residential properties.

I asked AI and suggestions were to check government records and public records so I'll do that, but wanted to see if anyone here has other suggestions.

My suggestion would be to cap your utilities at a certain amount and have Tenants pay anything over that amount.That will help you manage your expenses, and also allow Tenants to gage their usage each month, and make adjustments if they don't want to go over the allotted amount.As far as collection, provide the bill showing any overages and just have them pay for it along with their rent. 

It would cost a lot to get the planning approval and do a complete renovation of the 2 units.Can anyone suggest what would be my options at this point?

I’m particularly interested in methods that have worked well for you in terms of finding deals that aren’t listed on the MLS.Thanks in advance for your insights and suggestions!

Open to realtor suggestions if you have one you are happy with! 

:)I spoke to my attorney (From NYC), and he suggested forming the LLC in TN.

It's worth mentioning that I have the 1 or 2 bed options blocked from being booked on the weekends.All that said, I'm interested to see if anyone has any suggestions or ideas to help us with weekday bookings.

Any suggestions or am i missing a tool to do this with?