He only gave me an estimate (doesn't show work completed) for $5,000, even though the repairs were stated to cost $15,000, he said he lost other documents, when I ask him to retrieve them or allow me to retrieve them from repair company he won't.

that doesn't seem ideal - i think people should build up a track record before borrowing private money and putting it at risk.  

The city doesn't do much in the winter for residents, let alone the tourists (besides the basics like snow removal).

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

Otherwise with the dwindling tech sector in SF, and the remote work (2-3 days a week) that is most likely here to stay, it just doesn't seem like a strong mid term market to me.

The overall LTV (including all 3 mortgages) will be key and your selling point will need to be that the 2nd mortgage ($8k) will burn off in 2.5 years (based on your surprise that it was even out there, I'd recommend that you follow up in 2.5 years and ensure that it's been satisified, so that it doesn't surprise you again in the future).Does the $8k grant vest over the 5 years? 

Quote from @Lexi Lehman: Quote from @Derrick Lewis: I use TurboTenant for their other features (and tenants submit maintenance requests there), but haven't seen anything about a partnership with Lula until now.Lula doesn't cost anything for the property manager as a subscription normally, you just pay on a per-job basis.

It's nice to see the community showing support for STRs and pointing out that an STR doesn't solve any of the real problems.  

There are lots of REALLY GOOD investments and businesses out there - but that doesn’t mean they’re scalable. 

It doesn't work as well now because it's hard enough to be cash flow positive with prices + rates and where rents are at.